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13139-15-6

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13139-15-6 Usage

Chemical Properties

White Solid

Uses

Protected amino acid with antimicrobial activity.

Definition

ChEBI: A L-leucine derivative obtained by the substitution of a t-butoxycarbonyl group on the nitrogen atom.

Check Digit Verification of cas no

The CAS Registry Mumber 13139-15-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,1,3 and 9 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 13139-15:
(7*1)+(6*3)+(5*1)+(4*3)+(3*9)+(2*1)+(1*5)=76
76 % 10 = 6
So 13139-15-6 is a valid CAS Registry Number.
InChI:InChI=1/C11H21NO4/c1-7(2)6-8(9(13)14)12-10(15)16-11(3,4)5/h7-8H,6H2,1-5H3,(H,12,15)(H,13,14)/p-1/t8-/m1/s1

13139-15-6 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • TCI America

  • (B1187)  N-(tert-Butoxycarbonyl)-L-leucine Monohydrate  >99.0%(T)

  • 13139-15-6

  • 5g

  • 140.00CNY

  • Detail
  • TCI America

  • (B1187)  N-(tert-Butoxycarbonyl)-L-leucine Monohydrate  >99.0%(T)

  • 13139-15-6

  • 25g

  • 380.00CNY

  • Detail
  • Alfa Aesar

  • (A10647)  N-Boc-L-leucine hydrate, 99%   

  • 13139-15-6

  • 5g

  • 306.0CNY

  • Detail
  • Alfa Aesar

  • (A10647)  N-Boc-L-leucine hydrate, 99%   

  • 13139-15-6

  • 25g

  • 1002.0CNY

  • Detail
  • Sigma-Aldrich

  • (15450)  Boc-Leu-OH  ≥99.0% (HPLC)

  • 13139-15-6

  • 15450-5G-F

  • 223.47CNY

  • Detail
  • Sigma-Aldrich

  • (15450)  Boc-Leu-OH  ≥99.0% (HPLC)

  • 13139-15-6

  • 15450-25G-F

  • 772.20CNY

  • Detail
  • Sigma-Aldrich

  • (15450)  Boc-Leu-OH  ≥99.0% (HPLC)

  • 13139-15-6

  • 15450-100G-F

  • 2,260.44CNY

  • Detail

13139-15-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name N(α)-t-butoxycarbonyl-L-leucine

1.2 Other means of identification

Product number -
Other names BOC-L-LEUCINE-OH

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13139-15-6 SDS

13139-15-6Synthetic route

L-leucine
61-90-5

L-leucine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 25℃; for 23h;100%
With sodium hydroxide In 1,4-dioxane; water at 0℃;100%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 19h;99%
Boc-L-Leu-(Z)-ΔLeu-L-Ala-OMe
108460-59-9

Boc-L-Leu-(Z)-ΔLeu-L-Ala-OMe

A

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

B

(S)-2-(4-Methyl-2-oxo-pentanoylamino)-propionic acid

(S)-2-(4-Methyl-2-oxo-pentanoylamino)-propionic acid

Conditions
ConditionsYield
With McIlvaine buffer; 2-hydroxyethanethiol; papain (EC 3.4.22.2) at 35℃; for 24h; pH=8.0; Hydrolysis;A n/a
B 100%
L-leucine
61-90-5

L-leucine

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide for 4h; Ambient temperature;99%
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; pH=8 - 9;89.1%
L-leucine
61-90-5

L-leucine

1,2,2,2-Tetrachloroethyl tert-Butyl Carbonate
98015-52-2

1,2,2,2-Tetrachloroethyl tert-Butyl Carbonate

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 20℃; pH=9.75;95%
L-leucine
61-90-5

L-leucine

O-(tert-butyl) S-(pyridin-2-yl)carbonothioate
105678-24-8

O-(tert-butyl) S-(pyridin-2-yl)carbonothioate

A

2-Mercaptopyridine
2637-34-5

2-Mercaptopyridine

B

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide for 12h; Ambient temperature;A n/a
B 95%
L-leucine
61-90-5

L-leucine

tert-butyl pyridin-2-yl carbonate
89985-91-1

tert-butyl pyridin-2-yl carbonate

A

2-hydroxypyridin
142-08-5

2-hydroxypyridin

B

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide for 4h; Ambient temperature;A n/a
B 94%
Boc-Leu-ONbn
77163-64-5

Boc-Leu-ONbn

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran Ambient temperature;94%
(S)-(1-hydroxymethyl-3-methylbutyl)carbamic acid tert-butyl ester
82010-31-9

(S)-(1-hydroxymethyl-3-methylbutyl)carbamic acid tert-butyl ester

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid; sodium hydrogencarbonate; sodium bromide In water; acetone at 20℃; for 6h;92%
L-leucine
61-90-5

L-leucine

(N-hydroxy-5-norbornene-2,3-diformylimino)tert-butyl ester
64205-15-8

(N-hydroxy-5-norbornene-2,3-diformylimino)tert-butyl ester

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With tertiary amine In 1,4-dioxane; water for 3h;91%
2-tert-butoxycarbonylamino-4-methyl-pentanoic acid 3-methyl-but-2-enyl ester

2-tert-butoxycarbonylamino-4-methyl-pentanoic acid 3-methyl-but-2-enyl ester

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With cerium(III) chloride; sodium iodide In acetonitrile for 1.5h; Heating;91%
Boc-Leu-NHNHPh
17790-87-3

Boc-Leu-NHNHPh

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With oxygen In acetonitrile for 16h; tyrosinase, phosphate buffer pH 7;89%
With phosphate buffer; oxygen; tyrosinase In water; acetonitrile at 20℃; for 16h; pH=7.0;89%
L-leucine
61-90-5

L-leucine

tert-butyl (2,4-dioxo-3-azaspiro[5,5]undecan-3-yl) carbonate

tert-butyl (2,4-dioxo-3-azaspiro[5,5]undecan-3-yl) carbonate

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane; water at 25℃; for 15h;88%
t-butyl (S)-2-tert-butoxycarbonylamino-4-methylpentanoate
178432-61-6

t-butyl (S)-2-tert-butoxycarbonylamino-4-methylpentanoate

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With cerium(III) chloride; sodium iodide In acetonitrile for 5h; Heating;87%
With water; iodine In acetonitrile for 6h; Heating;82%
With trifluoroacetic acid
L-leucine
61-90-5

L-leucine

tert-butyl 2-oxo-1,3-oxazole-3(2H)-carboxylate
75844-68-7

tert-butyl 2-oxo-1,3-oxazole-3(2H)-carboxylate

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With dmap; triethylamine In 1,4-dioxane; water for 15h; Ambient temperature;85%
L-leucine
61-90-5

L-leucine

dimethylsulfonium methylsulfate

dimethylsulfonium methylsulfate

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With triethylamine In water Ambient temperature;75%
Boc-Leu-ΔLeu-Gly-OMe
193069-43-1

Boc-Leu-ΔLeu-Gly-OMe

A

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

B

(4-methyl-2-oxo-pentanoylamino)-acetic acid

(4-methyl-2-oxo-pentanoylamino)-acetic acid

Conditions
ConditionsYield
With McIlvaine buffer; 2-hydroxyethanethiol; papain (EC 3.4.22.2) at 35℃; for 24h; pH=8.0; Hydrolysis;A n/a
B 75%
(S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoic acid 2-trimethylsilanyl-ethoxymethyl ester

(S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoic acid 2-trimethylsilanyl-ethoxymethyl ester

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With magnesium bromide In dichloromethane for 2.5h; Ambient temperature; addition at -20 deg C, 0.5 h;71%
Boc-Leu-ΔLeu-Val-OMe
193069-44-2

Boc-Leu-ΔLeu-Val-OMe

A

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

B

(S)-3-Methyl-2-(4-methyl-2-oxo-pentanoylamino)-butyric acid

(S)-3-Methyl-2-(4-methyl-2-oxo-pentanoylamino)-butyric acid

Conditions
ConditionsYield
With McIlvaine buffer; 2-hydroxyethanethiol; papain (EC 3.4.22.2) at 35℃; for 24h; pH=8.0; Hydrolysis;A n/a
B 40%
Boc-Leu-ΔLeu-Leu-OMe

Boc-Leu-ΔLeu-Leu-OMe

A

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

B

(S)-4-Methyl-2-(4-methyl-2-oxo-pentanoylamino)-pentanoic acid

(S)-4-Methyl-2-(4-methyl-2-oxo-pentanoylamino)-pentanoic acid

Conditions
ConditionsYield
With McIlvaine buffer; 2-hydroxyethanethiol; papain (EC 3.4.22.2) at 35℃; for 24h; pH=8.0; Hydrolysis;A n/a
B 26%
N-(tert-butyloxycarbonyl) azide
1070-19-5

N-(tert-butyloxycarbonyl) azide

L-leucine
61-90-5

L-leucine

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With 1,4-dioxane; magnesium oxide
With hydroxide
With N,N,N',N'-tetramethylguanidine In N,N-dimethyl-formamide
L-leucine
61-90-5

L-leucine

tert-Butyl 4-nitrophenyl carbonate
13303-10-1

tert-Butyl 4-nitrophenyl carbonate

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With sodium hydroxide; tert-butyl alcohol
Kohlensaeure-(2,2-dimethyl-propylester)-(N-hydroxysuccinimidester)

Kohlensaeure-(2,2-dimethyl-propylester)-(N-hydroxysuccinimidester)

L-leucine
61-90-5

L-leucine

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane
tert-butyl (quinolin-8-yl)carbonate
18595-55-6

tert-butyl (quinolin-8-yl)carbonate

L-leucine
61-90-5

L-leucine

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide
L-leucine
61-90-5

L-leucine

tert-butyl fluoroformate
18595-34-1

tert-butyl fluoroformate

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane
L-leucine
61-90-5

L-leucine

1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate
16965-08-5

1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With triethylamine In tert-butyl alcohol
L-leucine
61-90-5

L-leucine

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
58632-95-4

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water Ambient temperature;
With triethylamine In 1,4-dioxane; water for 4h; Ambient temperature;
L-leucine
61-90-5

L-leucine

2,4-Dinitrophenyl-tert.-butylcarbonat
53639-37-5

2,4-Dinitrophenyl-tert.-butylcarbonat

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide
L-Leucine ethyl ester
2743-60-4

L-Leucine ethyl ester

tert-butyl cyanoformate
57022-34-1

tert-butyl cyanoformate

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
(i) hexane, (ii) aq. NaOH; Multistep reaction;
piperidine
110-89-4

piperidine

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

(S)-tert-butyl 4-methyl-1-oxo-1-(piperidin-1-yl)pentan-2-ylcarbamate
78664-62-7

(S)-tert-butyl 4-methyl-1-oxo-1-(piperidin-1-yl)pentan-2-ylcarbamate

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 1h;100%
With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran for 4h; Ambient temperature;90%
80%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Boc-Leu-ONSu
3392-09-4

Boc-Leu-ONSu

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 0 - 4℃;100%
With dicyclohexyl-carbodiimide In 1,4-dioxane Ambient temperature;93%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 20℃; for 18h;93%
1,1,1-trichloroethanol
115-20-8

1,1,1-trichloroethanol

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Nα-(tert-butoxycarbonyl)-L-leucine 2',2',2'-trichloroethyl ester
162307-38-2

Nα-(tert-butoxycarbonyl)-L-leucine 2',2',2'-trichloroethyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrachloromethane; dichloromethane for 3h;100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 18h; Ambient temperature;93%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide
87694-50-6

N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide

Conditions
ConditionsYield
Stage #1: N-tert-butoxycarbonyl-L-leucine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.25h; Inert atmosphere;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With 4-methyl-morpholine In dichloromethane at 0 - 25℃; for 14h; Inert atmosphere;
100%
Stage #1: N-tert-butoxycarbonyl-L-leucine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.25h; Inert atmosphere;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With 4-methyl-morpholine In dichloromethane at 25℃; for 14h; Inert atmosphere;
100%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane100%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

(S)-2-Amino-1-(4-benzyl-piperidin-1-yl)-3-methyl-butan-1-one; hydrochloride
118792-26-0

(S)-2-Amino-1-(4-benzyl-piperidin-1-yl)-3-methyl-butan-1-one; hydrochloride

{(S)-1-[(S)-1-(4-Benzyl-piperidine-1-carbonyl)-2-methyl-propylcarbamoyl]-3-methyl-butyl}-carbamic acid tert-butyl ester
118792-33-9

{(S)-1-[(S)-1-(4-Benzyl-piperidine-1-carbonyl)-2-methyl-propylcarbamoyl]-3-methyl-butyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 4℃;100%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

(S)-(1-hydroxymethyl-3-methylbutyl)carbamic acid tert-butyl ester
82010-31-9

(S)-(1-hydroxymethyl-3-methylbutyl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
With borane-THF In tetrahydrofuran 1.) 0 deg C, 1 h; 2.) RT; 3.) 0 deg C, 1 h;100%
Stage #1: N-tert-butoxycarbonyl-L-leucine With 4-methyl-morpholine; tert-butyl chloroformate In 1,2-dimethoxyethane
Stage #2: With sodium tetrahydroborate In 1,2-dimethoxyethane; water at -15℃; Further stages.;
96%
With borane-THF In tetrahydrofuran for 1h; Ambient temperature;91%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride
3945-69-5

4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

2-tert-butoxycarbonylamino-4-methyl-pentanoic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester
345911-00-4

2-tert-butoxycarbonylamino-4-methyl-pentanoic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester

Conditions
ConditionsYield
In 1,2-dimethoxyethane at 0℃; for 3h; Condensation;100%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

3-(2'-Hydroxy-5'-benzyloxy-4',6'-dimethylphenyl)-3,3-dimethyl-1-propanol
157547-47-2

3-(2'-Hydroxy-5'-benzyloxy-4',6'-dimethylphenyl)-3,3-dimethyl-1-propanol

2-tert-butoxycarbonylamino-4-methyl-pentanoic acid 3-(3-benzyloxy-6-hydroxy-2,4-dimethyl-phenyl)-3-methyl-butyl ester
264888-34-8

2-tert-butoxycarbonylamino-4-methyl-pentanoic acid 3-(3-benzyloxy-6-hydroxy-2,4-dimethyl-phenyl)-3-methyl-butyl ester

Conditions
ConditionsYield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 5h; Acylation;100%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

β-hydroxyphenylalanine methyl ester hydrochloride
80182-99-6

β-hydroxyphenylalanine methyl ester hydrochloride

Boc-L-Leu-DL-Phe(β-OH)-OMe
896735-84-5

Boc-L-Leu-DL-Phe(β-OH)-OMe

Conditions
ConditionsYield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;100%
With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

4,6-O-di(tert-butyl)silanediyl-D-glucal
191593-14-3

4,6-O-di(tert-butyl)silanediyl-D-glucal

3-O-(N-tert-butoxycarbonyl-L-leucyl)-4,6-O-di-tert-butylsilanediyl-D-glucal

3-O-(N-tert-butoxycarbonyl-L-leucyl)-4,6-O-di-tert-butylsilanediyl-D-glucal

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane100%
(S)-Pyrrolidine-2-carboxylic acid (3-carbamoyl-phenyl)-amide
1006030-39-2

(S)-Pyrrolidine-2-carboxylic acid (3-carbamoyl-phenyl)-amide

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

{(S)-1-[(S)-2-(3-Carbamoyl-phenylcarbamoyl)-pyrrolidine-1-carbonyl]-3-methyl-butyl}-carbamic acid tert-butyl ester
886847-55-8

{(S)-1-[(S)-2-(3-Carbamoyl-phenylcarbamoyl)-pyrrolidine-1-carbonyl]-3-methyl-butyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With 4-methyl-morpholine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane; N,N-dimethyl-formamide100%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

(3S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-methylhex-5-en-3-ol
168777-81-9

(3S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-methylhex-5-en-3-ol

(1S,2R)-1-[2-(tert-butyldimethylsilanyloxy)ethyl]-2-(methyl)but-3-enyl (2S)-2-tert-butoxycarbonylamino-4-methylpentanoate
916452-48-7

(1S,2R)-1-[2-(tert-butyldimethylsilanyloxy)ethyl]-2-(methyl)but-3-enyl (2S)-2-tert-butoxycarbonylamino-4-methylpentanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h;100%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

ethyl 2-(benzylamino)acetate
6436-90-4

ethyl 2-(benzylamino)acetate

(3S)-1-benzyl-3-isobutylpiperazine-2,5-dione
502482-25-9

(3S)-1-benzyl-3-isobutylpiperazine-2,5-dione

Conditions
ConditionsYield
Stage #1: N-tert-butoxycarbonyl-L-leucine; ethyl 2-(benzylamino)acetate With dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃; for 3.25h;
Stage #2: With hydrogenchloride In dichloromethane for 4h;
100%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

L-leucine
61-90-5

L-leucine

Conditions
ConditionsYield
With water at 170℃; for 0.05h; Microwave irradiation;100%
With tetradecyl(trihexyl)phosphonium bistriflamide; trifluoroacetic acid at 130℃; for 0.166667h; Ionic liquid;98%
Multi-step reaction with 3 steps
1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate
2: trifluoroacetic acid
3: E. coli BL21 Star (DE3) S30 extract / aq. buffer / 6 h / 37 °C / pH 7.5
View Scheme
Multi-step reaction with 3 steps
1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate
2: trifluoroacetic acid
3: E. coli BL21 Star (DE3) S30 extract / aq. buffer / 6 h / 37 °C / pH 7.5
View Scheme
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 2h;
1-(tert-butoxycarbonyl)-L-proline
15761-39-4

1-(tert-butoxycarbonyl)-L-proline

t-Boc-L-valine
13734-41-3

t-Boc-L-valine

N-(tert-butyloxycarbonyl)-L-isoleucine
13139-16-7

N-(tert-butyloxycarbonyl)-L-isoleucine

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

H-Hphe-Leu-Ile-Ile-Leu-Val-Pro-Pro-Phe-OH
1187223-35-3

H-Hphe-Leu-Ile-Ile-Leu-Val-Pro-Pro-Phe-OH

Conditions
ConditionsYield
Stage #1: Boc-L-homophenylalanine solid phase reaction;
Stage #2: With trifluoroacetic acid In dichloromethane solid phase reaction;
Stage #3: 1-(tert-butoxycarbonyl)-L-proline; t-Boc-L-valine; N-(tert-butyloxycarbonyl)-L-isoleucine; N-tert-butoxycarbonyl-L-leucine; N-tert-butoxycarbonyl-L-phenylalanine Further stages;
100%
1-(tert-butoxycarbonyl)-L-proline
15761-39-4

1-(tert-butoxycarbonyl)-L-proline

t-Boc-L-valine
13734-41-3

t-Boc-L-valine

N-(tert-butyloxycarbonyl)-L-isoleucine
13139-16-7

N-(tert-butyloxycarbonyl)-L-isoleucine

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

H-Ile-Ile-Leu-Val-Pro-Pro-Hphe-Hphe-Leu-OH
1187223-36-4

H-Ile-Ile-Leu-Val-Pro-Pro-Hphe-Hphe-Leu-OH

Conditions
ConditionsYield
Stage #1: N-tert-butoxycarbonyl-L-leucine solid phase reaction;
Stage #2: With trifluoroacetic acid In dichloromethane solid phase reaction;
Stage #3: 1-(tert-butoxycarbonyl)-L-proline; t-Boc-L-valine; N-(tert-butyloxycarbonyl)-L-isoleucine; N-tert-butoxycarbonyl-L-phenylalanine; Boc-L-homophenylalanine Further stages;
100%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

6-ethynyl-3,3-dimethoxyhexahydrofuro[3,2-b]pyrrole-4-carboxylic acid tert-butyl ester
1219603-58-3

6-ethynyl-3,3-dimethoxyhexahydrofuro[3,2-b]pyrrole-4-carboxylic acid tert-butyl ester

C21H34N2O6
1219603-61-8

C21H34N2O6

Conditions
ConditionsYield
Stage #1: 6-ethynyl-3,3-dimethoxyhexahydrofuro[3,2-b]pyrrole-4-carboxylic acid tert-butyl ester With methanol; acetyl chloride at 20℃; Cooling in ice;
Stage #2: N-tert-butoxycarbonyl-L-leucine With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 3.25h;
100%
2,4-bis(docosyloxy)benzyl alcohol
931120-51-3

2,4-bis(docosyloxy)benzyl alcohol

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

C62H115NO6
1258442-24-8

C62H115NO6

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃;100%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

3,5-di(docosyloxy)benzyl alcohol
955095-32-6

3,5-di(docosyloxy)benzyl alcohol

C62H115NO6
1258442-25-9

C62H115NO6

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃;100%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

(3,4,5-trioctadecyloxyphenyl)methan-1-ol
233281-31-7

(3,4,5-trioctadecyloxyphenyl)methan-1-ol

C72H135NO7
1258442-23-7

C72H135NO7

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃;100%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Propargylamine
2450-71-7

Propargylamine

tert-Butyl [(2S)-1-(thynylamino)-4-methyl-1-oxopentan-2-yl]carbamate
1268671-03-9

tert-Butyl [(2S)-1-(thynylamino)-4-methyl-1-oxopentan-2-yl]carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane for 2h; Inert atmosphere; Reflux;100%
With benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane at 20℃; for 2h;90%
Stage #1: N-tert-butoxycarbonyl-L-leucine With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In dichloromethane for 0.166667h; Cooling with ice;
Stage #2: Propargylamine With triethylamine In dichloromethane at 20℃; for 24h;
82%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

(R)-4-amino-2-methyl-1-butanol
44565-27-7, 44565-28-8, 64070-19-5, 88390-32-3

(R)-4-amino-2-methyl-1-butanol

[1-(4-hydroxy-3-methylbutylcarbamoyl)-3-methylbutyl]-carbamic acid tert-butyl ester
1265404-73-6

[1-(4-hydroxy-3-methylbutylcarbamoyl)-3-methylbutyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;100%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

methyl 3-aminopropanoate hydrochloride
3196-73-4

methyl 3-aminopropanoate hydrochloride

3-(2-tert-butoxycarbonylamino-4-methylpentanoylamino)-propionic acid methyl ester
1160927-49-0

3-(2-tert-butoxycarbonylamino-4-methylpentanoylamino)-propionic acid methyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 5h; Inert atmosphere;100%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

3-(1-[3-ammoniopropyl]-1H-indol-3-yl)-4-(3,4,5-trimethoxyphenyl)-maleinimide-chloride
1312545-25-7

3-(1-[3-ammoniopropyl]-1H-indol-3-yl)-4-(3,4,5-trimethoxyphenyl)-maleinimide-chloride

tert-butyl 1-(3-(3-(2,5-dioxo-4-(3,4,5-trimethoxyphenyl)-2,5-dihydro-1H-pyrrol-3-yl)-1H-indol-1-yl)propylamino)-4-methyl-1-oxopentan-2-ylcarbamate
1383842-05-4

tert-butyl 1-(3-(3-(2,5-dioxo-4-(3,4,5-trimethoxyphenyl)-2,5-dihydro-1H-pyrrol-3-yl)-1H-indol-1-yl)propylamino)-4-methyl-1-oxopentan-2-ylcarbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 24h;100%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

2-methoxy-5-(2,3,4-trimethoxy-7-oxo-6,7-dihydro-5H-benzo[7]annulen-9-yl)benzenaminium chloride

2-methoxy-5-(2,3,4-trimethoxy-7-oxo-6,7-dihydro-5H-benzo[7]annulen-9-yl)benzenaminium chloride

tert-butyl 1-(5-(6,7-dihydro-2,3,4-trimethoxy-7-oxo-5H-benzo[7]annulen-9-yl)-2-methoxyphenylcarbamoyl)-3-methylbutylcarbamate

tert-butyl 1-(5-(6,7-dihydro-2,3,4-trimethoxy-7-oxo-5H-benzo[7]annulen-9-yl)-2-methoxyphenylcarbamoyl)-3-methylbutylcarbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;100%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

8,9-dihydro-5-(3-hydroxy-4-methoxyphenyl)-1,2,3-trimethoxybenzo[7]annulen-7-one

8,9-dihydro-5-(3-hydroxy-4-methoxyphenyl)-1,2,3-trimethoxybenzo[7]annulen-7-one

C32H41NO9

C32H41NO9

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine; 2,6-Dichlorobenzoyl chloride In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;100%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

(3S)-3-Amino-N-ethyl-2-hydroxy-4-phenylbutanamide hydrochloride

(3S)-3-Amino-N-ethyl-2-hydroxy-4-phenylbutanamide hydrochloride

tert-butyl ((2S)-1-((4-(ethylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)carbamate

tert-butyl ((2S)-1-((4-(ethylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;100%
methyl Nω-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl)-L-argininate

methyl Nω-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl)-L-argininate

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Boc-Leu-Arg(Pbf)-OMe

Boc-Leu-Arg(Pbf)-OMe

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran Cooling with ice;100%

13139-15-6Relevant articles and documents

Synthesis, antimicrobial potency with in silico study of Boc-leucine-1,2,3-triazoles

Ghule, Vikas D.,Kumar, Ashwani,Lal, Kashmiri,Naveen,Tittal, Ram Kumar,Yadav, Pinki

, (2020)

A library of N-Boc protected Leucine-linked 1,4-disubstituted 1,2,3-triazoles was synthesized and fully characterized, in high yield via copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction. In vitro antibacterial activity showed that compound 4h found to be more potent than the reference drug Ciprofloxacin (MIC: 0.0196 μmol/mL) against tested bacterial strains S. entrica, B. subtilis, S. aureus, E. coli and P. auroginosa with MIC: 0.0148, 0.0074, 0.0148, 0.0074, and 0.0074 μmol/mL, respectively and antifungal activity with MIC: 0.0148 μmol/mL as compared to reference drug Fluconazole (MIC: 0.0102 μmol/mL) against A. niger and C. albicans fungal strains. Further, the molecular docking study on 4h and its predecessor alkyne 3 by choosing E. coli topoisomerase II, DNA Gyrase (PDB ID: 1KZN) showed better binding with triazole than alkyne and these results were supported by DFT study using B3LYP/6-311G(d,p) basis set.

Optical resolution of N-(t-butoxycarbonyl)leucine through mixed ligand complex formation with (R)-N-(2-pyridylmethyl)pipecolatocopper(II)

Yajima, Tatsuo,Fukushima, Takeo,Yamada, Atsuya,Shiraiwa, Tadashi

, p. 451 - 455 (2017)

A copper(II) complex of (R)-N-(2-pyridylmethyl)pipecolate (pmpi) was prepared, and its structure was revealed by X-ray crystal structure analysis. Mixed ligand complexes were then prepared from this complex and (R)- and (S)-N-(t-butoxycarbonyl)leucinate (BocLeu). The (R)-BocLeu complex is less soluble in aqueous acetonitrile and more soluble in acetone than the (S)-BocLeu complex, and the reason was discussed on the basis of their structures. Recrystallization of the reaction mixture consisting of Cu(II) ion, pmpi, and (RS)-BocLeu from aqueous acetonitrile gave the (R)-BocLeu complex and that from acetone gave the (S)-BocLeu complex.

Synthesis, in vitro and in vivo biological evaluation of dihydroartemisinin derivatives with potential anti-Toxoplasma gondii agents

Deng, Hao,Huang, Xing,Jin, Chun-Mei,Jin, Chunmei,Quan, Zhe-Shan

, (2020)

In this study, four series of dihydroartemisinin derivatives were designed, synthesized, and evaluated for anti-toxoplasma gondii activity, and calculated the selectivity index (SI). It was the higher the SI, the better the effect of this compound against Toxoplasma gondii. Our goal was to filter out compounds that were bigger SI than the lead compound. The compound with the highest SI was selected for the anti-toxoplasmosis test in mice in vivo. Among the synthesized compounds, the (3R,5aS,6R,8aS,9R,12R,12aR)-3,6,9-trimethyl-decahydro-12H-3,12-epoxy[1,2]di-oxepino[4,3 -i]isochromen-10-yl-(te-rt-butoxycarbonyl)-L-alaninate (A2) exhibited the most potent anti-T. gondii activity and low cytotoxicity (SI: 6.44), yielding better results than the lead compound DHA (SI: 1.00) and the clinically used positive-control drug spiramycin (SI: 0.72) in vitro. Furthermore, compound A2 had better growth inhibitory effects on T. gondii in vivo than spiramycin did and significantly reduced the number of tachyzoites in the peritoneal cavity of mice (P 0.01). The evaluation of the data generated in the T. gondii mouse infection model indicates that compound A2 treatment was a good inhibitor of T. gondii in vivo and that it was effective in relieving the liver damage induced by T. gondii. In addition, the results of a docking study revealed that A2 could become a better T. gondii calcium-dependent protein kinase1 (TgCDPK1) inhibitor. For this reason, compound A2 has potential as an anti-parasitic drug. Further studies are required to elucidate the mechanism of the action of compound A2, as well as to develop drug delivery systems for patients.

Synthesis and bioactivities study of new antibacterial peptide mimics: The dialkyl cationic amphiphiles

Zhang, En,Bai, Peng-Yan,Cui, De-Yun,Chu, Wen-Chao,Hua, Yong-Gang,Liu, Qin,Yin, Hai-Yang,Zhang, Yong-Jie,Qin, Shangshang,Liu, Hong-Min

, p. 1489 - 1509 (2018)

The emergence of infectious diseases caused by pathogenic bacteria is widespread. Therefore, it is urgently required to enhance the development of novel antimicrobial agents with high antibacterial activity and low cytotoxicity. A series of novel dialkyl cationic amphiphiles bearing two identical length lipophilic alkyl chains and one non-peptidic amide bond were synthesized and tested for antimicrobial activities against both Gram-positive and Gram-negative bacteria. Particular compounds synthesized showed excellent antibacterial activity toward drug-sensitive bacteria such as S. aureus, E. faecalis, E. coli and S. enterica, and clinical isolates of drug-resistant species such as methicillin-resistant S. aureus (MRSA), KPC-producing and NDM-1-producing carbapenem-resistant Enterobacteriaceae (CRE). For example, the MIC values of the best compound 4g ranged from 0.5 to 2 μg/mL against all these strains. Moreover, these small molecules acted rapidly as bactericidal agents, and functioned primarily by permeabilization and depolarization of bacterial membranes. Importantly, these compounds were difficult to induce bacterial resistance and can potentially combat drug-resistant bacteria. Thus, these compounds can be developed into a new class of antibacterial peptide mimics against Gram-positive and Gram-negative bacteria, including drug-resistant bacterial strains.

-

Grzonka,Z.,Lammek,B.

, p. 661 - 662 (1974)

-

Water-soluble gambogic acid PEGylated prodrugs: Synthesis, characterization, physicochemical properties and in vitro hydrolysis

Tang, Xiaoyan,Zhang, Peng,Ye, Hai,Zhang, Can,Shen, Wenbin,Ping, Qineng

, p. 711 - 717 (2008)

A series of poly(ethylene glycol) (PEG) prodrugs of gambogic acid (GA) with different molecular weight which used L-leucine as spacer were synthesized and characterized by FT-IR, 1H NMR and TOF MS. Drug loading capability, analyzed by UV spectrum, was 17.48, 9.26, 3.99, and 1.79%, aqueous solubility of the prodrugs was determined to be 1750, 1250, 800, and 645 mg/ml, respectively. The drug release from prodrugs was investigated under simulated in vivo conditions whose half-time (t1/2) in plasma ranged from 1.26 to 6.12 h. The effect of temperature on drug release was studied at four different temperatures and activation energy was determined as well. The stability of the prodrugs was improved in parallel with increasing molecular weight of PEG while prodrug yields and drug loading capability were reduced.

Enantioselective Deaminative Alkylation of Amino Acid Derivatives with Unactivated Olefins

Cai, Yue-Ming,Martin, Ruben,Rui, Xi-Yan,Shang, Ming,Sun, Shang-Zheng,Wang, Jia-Bao,Yao, Hong-Qing,Zhang, De-Liang

supporting information, p. 1130 - 1137 (2022/02/05)

Herein, we report the first Ni-catalyzed enantioselective deaminative alkylation of amino acid and peptide derivatives with unactivated olefins. Key for success was the discovery of a new sterically encumbered bis(oxazoline) ligand backbone, thus offering a de novo technology for accessing enantioenriched sp3-sp3 linkages via sp3 C-N functionalization. Our protocol is distinguished by its broad scope and generality across a wide number of counterparts, even in the context of late-stage functionalization. In addition, an enantioselective deaminative remote hydroalkylation reaction of unactivated internal olefins is within reach, thus providing a useful entry point for forging enantioenriched sp3-sp3 centers at remote sp3 C-H sites.

Elucidation of absolute configuration of ophiorrhiside a by comparison of ecd spectra with that of model chiral compound having a 1,2,3,4-tetrahydro-β-carbolin-3-one skeleton

Onozawa, Tadayoshi,Kogure, Noriyuki,Takayama, Hiromitsu,Kitajima, Mariko

, p. 35 - 43 (2021/02/12)

A chiral 1,2,3,4-tetrahydro-β-carbolin-3-one having a substituent at C-1 was synthesized from L-leucine and used to elucidate the absolute configuration at C-3 of ophiorrhiside A, a monoterpenoid glucoindole alkaloid.

α-Amino Acids and α,β-Dipeptides Intercalated into Hydrotalcite: Efficient Catalysts in the Asymmetric Michael Addition Reaction of Aldehydes to N-Substituted Maleimides

Landeros, José M.,Cruz-Hernández, Carlos,Juaristi, Eusebio

supporting information, p. 5117 - 5126 (2021/09/13)

In this work, a series of α-amino acids (L-Phe, D-Phe, L-Trp) and several α,β-dipeptides (H2N-L-Val-N-Bn-β-Ala-COOH and H2N-L-Leu-N-Bn-β-Ala-COOH) intercalated into hydrotalcite (Mg/Al, x=0.333) were prepared by high speed ball milling (HSBM) assisted rehydration/reconstruction methods, followed by sonication and mechanical stirring. All organic-inorganic hybrid samples were characterized by powder X-ray diffraction (XRD) and FTIR-ATR spectroscopy. The catalytic activity of the resulting hydrotalcite-supported materials (natural and hybrid) was evaluated in the asymmetric Michael addition reaction of α,α-disubstituted-aldehydes to N-substituted-maleimides. Pristine (HTS), calcined (HTC) and water-reconstructed (HTR-l) hydrotalcite-derived materials exhibited very low catalytic activities, affording racemic mixtures of the anticipated Michael adduct. By contrast, hybrid materials showed better activities, especially HTR-α-amino acid catalysts afforded Michael products in up to 94 % yield and with rather high enantioselectivity (enantiomeric ratio (e.r.) up to 99 : 1) at room temperature under neat reaction conditions. The effect of solvents and Br?nsted basic or acidic additives was evaluated using the best hybrid catalyst, HTR-L-Phe. In addition, recycling and reuse of the catalyst (up to 4 cycles) and large-scale experiments was successfully carried out.

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