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(2S)-2-acetamido-3-phenylpropanoate
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2018-61-3 Usage

Purification Methods

N-Acetyl-L-phenylalanine is recrystallised from H2O, 20% MeOH/H2O, or CHCl3; dry and store it at 4o. The (DL)-isomer crystallises from H2O, Me2CO, EtOAc, or CHCl3 with m 152-154o and the solubilities in w% at 25o are 0.73 (H2O), 4.3 (Me2CO), 0.79 (EtOAc) and 0.34 (CHCl3) [Kerr & Niemann J Org Chem 23 893 1958, Overby & Ingersoll J Am Chem Soc 73 3363 1951, L: Fu et al. J Am Chem Soc 76 6057 1954, Bender & Glasson J Am Chem Soc 81 1591 1959]. [Beilstein 14 I 238, 4 IV 1575.]

Chemical Properties

white to off-white fine cryst. powder or needles

Definition

ChEBI: The N-acetyl derivative of L-phenylalanine.
InChI:InChI=1/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/p-1/t10-/m0/s1

2018-61-3 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (A1541)  N-Acetyl-L-phenylalanine  >99.0%(T) 2018-61-3 5g 370.00CNY Detail
TCI America (A1541)  N-Acetyl-L-phenylalanine  >99.0%(T) 2018-61-3 25g 1,130.00CNY Detail
Alfa Aesar (B23812)  N-Acetyl-L-phenylalanine, 99%    2018-61-3 1g 188.0CNY Detail
Alfa Aesar (B23812)  N-Acetyl-L-phenylalanine, 99%    2018-61-3 5g 511.0CNY Detail
Alfa Aesar (B23812)  N-Acetyl-L-phenylalanine, 99%    2018-61-3 25g 2029.0CNY Detail
Aldrich (857459)  N-Acetyl-L-phenylalanine  ReagentPlus®, 99% 2018-61-3 857459-1G 288.99CNY Detail
Aldrich (857459)  N-Acetyl-L-phenylalanine  ReagentPlus®, 99% 2018-61-3 857459-5G 507.55CNY Detail
Vetec (V900630)  N-Acetyl-L-phenylalanine  Vetec reagent grade, 98% 2018-61-3 V900630-1G 85.41CNY Detail
Vetec (V900630)  N-Acetyl-L-phenylalanine  Vetec reagent grade, 98% 2018-61-3 V900630-5G 194.22CNY Detail

2018-61-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name N-acetyl-L-phenylalanine

1.2 Other means of identification

Product number -
Other names N-Acetyl-l-Phenylalanine

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:2018-61-3 SDS

2018-61-3Synthetic route

N-acetamido cinnamic acid
55065-02-6, 64590-80-3, 5469-45-4

N-acetamido cinnamic acid

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With hydrogen; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate; triethylamine; (2R,2'R)-bis(diphenylphosphino)-(1R,1'R)-dicyclopentane In tetrahydrofuran at 20℃; under 750.075 Torr; for 24h;100%
With hydrogen; (1+)*BF4(1-) In ethanol; benzene under 20 Torr;99%
With hydrogen; Rh(nbd)(1)BF4 In dichloromethane at 50℃; under 38787.1 Torr; for 12h;99%
N-acetyl dehydrophenylalanine methyl ester
52386-78-4

N-acetyl dehydrophenylalanine methyl ester

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With hydrogen; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate In methanol at 22℃; under 38000 Torr;100%
ethyl N-acetyl-(L)-phenylalaninate
2361-96-8

ethyl N-acetyl-(L)-phenylalaninate

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With ammonium bicarbonate; water In dichloromethane for 12h; α-chymotrypsin;100%
With caesium carbonate In methanol; water for 24h;99%
With caesium carbonate In methanol; water for 24h; Product distribution; other alcohols;99%
With α-chymotrypsin In water at 25℃; Rate constant; pH 7.0-7.8;
With bis-Tris propane buffer; calcium chloride at 25℃; Rate constant;
L-phenylalanine
63-91-2

L-phenylalanine

acetic anhydride
108-24-7

acetic anhydride

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
In water for 0.0666667h; Irradiation;98%
With sodium hydroxide In water pH=10; Cooling with ice;93%
With sodium hydroxide In water at 20℃; for 3h; pH=8; Concentration;93%
(S)-N-acetylphenylalanine
3618-96-0

(S)-N-acetylphenylalanine

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With magnesium iodide In tetrahydrofuran at 120℃; for 1h; Inert atmosphere; Microwave irradiation; Sealed tube; chemoselective reaction;98%
With sodium carbonate In methanol; water for 4h;88%
With sodium carbonate In methanol; water for 4h; Product distribution; other alkali carbonates;88%
With water In N,N-dimethyl-formamide carbonate buffer (pH=10.5); α-chymotrypsin-cat. hydrolysis (spec. activity);
L-phenylalanine
63-91-2

L-phenylalanine

acetyl chloride
75-36-5

acetyl chloride

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
In water at 110℃; for 0.0833333h; Microwave irradiation; Green chemistry; chemoselective reaction;97%
With pyridine at 20℃;84.6%
Rh(COD)2 BF4

Rh(COD)2 BF4

N-acetamido cinnamic acid
55065-02-6, 64590-80-3, 5469-45-4

N-acetamido cinnamic acid

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With hydrogen In tetrahydrofuran97%
(Z)-2-acetamidocinnamic acid

(Z)-2-acetamidocinnamic acid

pyrographite
7440-44-0

pyrographite

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With hydrogen In methanol; benzene96.2%
N-acetylphenylalanine methyl ester
21156-62-7, 3618-96-0, 62436-70-8

N-acetylphenylalanine methyl ester

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With sodium hydroxide In water Alcalase, pH 7.5;93.7%
With cross-linked yeast cells (Saccharomyces cerevisiae); water In dimethyl sulfoxide at 30℃; for 48h;
N-acetylphenylalanine methyl ester
21156-62-7, 3618-96-0, 62436-70-8

N-acetylphenylalanine methyl ester

A

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

B

(R)-N-acetylphenylalanine methyl ester
21156-62-7

(R)-N-acetylphenylalanine methyl ester

Conditions
ConditionsYield
With sodium hydroxide; phosphate buffer; pronase EC 3.4.24.4 In tetrahydrofuran Ambient temperature;A 86%
B 93%
Yield given. Yields of byproduct given;
With Lecitase Ultra; water; calcium chloride at 30℃; for 12h; pH=8.5; aq. buffer; Enzymatic reaction; enantioselective reaction;
L-phenylalanine
63-91-2

L-phenylalanine

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With hydrogenchloride; acetic anhydride In sodium hydrogencarbonate; ethyl acetate90.3%
With hydrogenchloride; acetic anhydride; triethylamine In water
Multi-step reaction with 2 steps
1: dichloromethane / 16 h / 20 °C
2: dichloromethane / 16.5 h / -40 - 20 °C
View Scheme
2-(N-acetylamino)cinnamic acid
55065-02-6, 64590-80-3, 5469-45-4

2-(N-acetylamino)cinnamic acid

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; (3S,3'S)-3,3'-di-tert-butyl-2,2',3,3'-tetrahydro-4,4'-bibenzo[d][1,3]oxaphosphole; hydrogen In methanol at 20℃; under 5171.62 Torr; for 24h; Autoclave; enantioselective reaction;90%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; C48H42Fe2O2; hydrogen In methanol at 20℃; under 7600.51 Torr; for 24h; optical yield given as %ee;88%
With hydrogen In ethanol Product distribution; Ambient temperature; various catalysts;
(S)-N-acetylphenylalanine tert-butyl ester
68277-06-5

(S)-N-acetylphenylalanine tert-butyl ester

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With sulfuric acid In dichloromethane at 20℃; for 6h;90%
L-phenylalanine
63-91-2

L-phenylalanine

thioacetic acid
507-09-5

thioacetic acid

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate In methanol at 20℃; for 0.0833333h;90%
N-acetamido cinnamic acid
55065-02-6, 64590-80-3, 5469-45-4

N-acetamido cinnamic acid

A

(R)-N-acetylphenylalanin
10172-89-1

(R)-N-acetylphenylalanin

B

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With [Rh(cod)(Xylophos)](1+)*BF4(1-); hydrogen In methanol at 19.85℃; under 760 Torr; for 6h;A 11%
B 89%
With hydrogen; (1+); Dowex HCR-S In methanol; water at 50℃; under 15001.2 Torr; Product distribution; other rhodium(I)-complexes, various reaction conditions: time, pressure and temperatures; other derivatives of acetamidoacryl acid;
With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; optically active phosphine In methanol at 20 - 30℃; under 825.07 Torr; for 72h; Product distribution; various di- and triphosphines, other temperatures and times;
alpha-acetaminocinnamic acid
103989-08-8, 104787-34-0

alpha-acetaminocinnamic acid

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
82%
L-phenylalanine
63-91-2

L-phenylalanine

acetic acid
64-19-7

acetic acid

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With (1-methyl-3-(3-sulfopropyl)-1H-imidazol-3-ium)3[PW12O403-] In neat (no solvent) at 120℃; for 0.333333h; Green chemistry;73%
L-lysine n-butyl ester
2885-12-3

L-lysine n-butyl ester

ethyl N-acetyl-(L)-phenylalaninate
2361-96-8

ethyl N-acetyl-(L)-phenylalaninate

A

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

B

(S)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-6-amino-hexanoic acid butyl ester

(S)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-6-amino-hexanoic acid butyl ester

Conditions
ConditionsYield
With Tris-HCl buffer; α-chymotropsin In water; N,N-dimethyl-formamide at 25℃; pH 9;A n/a
B 67%
L-phenylalanine
63-91-2

L-phenylalanine

(4-acetoxyphenyl)-dimethylsulphonium methyl sulphate
108965-56-6

(4-acetoxyphenyl)-dimethylsulphonium methyl sulphate

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With triethylamine In water for 4h; Ambient temperature; pH=10.0;63%
L-Lysine ethyl ester
4117-33-3

L-Lysine ethyl ester

ethyl N-acetyl-(L)-phenylalaninate
2361-96-8

ethyl N-acetyl-(L)-phenylalaninate

A

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

B

(S)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-6-amino-hexanoic acid ethyl ester

(S)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-6-amino-hexanoic acid ethyl ester

Conditions
ConditionsYield
With Tris-HCl buffer; α-chymotropsin In water; N,N-dimethyl-formamide pH 9;A n/a
B 53%
With α-chymotrypsin at 25℃; for 0.05h; Product distribution; various buffer and pH;
ethyl N-acetyl-DL-phenylalaninate
4134-09-2

ethyl N-acetyl-DL-phenylalaninate

A

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

B

(R)-ethyl N-acetylphenylalanine
2361-96-8, 4134-09-2, 57772-79-9, 20918-84-7

(R)-ethyl N-acetylphenylalanine

Conditions
ConditionsYield
With ammonium bicarbonate; water In dichloromethane for 18h; α-chymotrypsin;A 50%
B 50%
A 50%
B 50%
In ethanol; water at 35℃; for 48h; Yield given;
ethyl N-acetyl-DL-phenylalaninate
4134-09-2

ethyl N-acetyl-DL-phenylalaninate

A

(R)-N-acetylphenylalanin
10172-89-1

(R)-N-acetylphenylalanin

B

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

C

(R)-ethyl N-acetylphenylalanine
2361-96-8, 4134-09-2, 57772-79-9, 20918-84-7

(R)-ethyl N-acetylphenylalanine

Conditions
ConditionsYield
With water In ethanol at 25℃; for 2h; Microbiological reaction; optical yield given as %ee; enantioselective reaction;A n/a
B n/a
C 45%
at 35℃; for 48h; in the present of Saccharomyces cerevisiae Hansen; Yield given. Yields of byproduct given;
lysine benzyl ester p-toluenesulfonate salt
42406-73-5

lysine benzyl ester p-toluenesulfonate salt

ethyl N-acetyl-(L)-phenylalaninate
2361-96-8

ethyl N-acetyl-(L)-phenylalaninate

A

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

B

(S)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-6-amino-hexanoic acid benzyl ester

(S)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-6-amino-hexanoic acid benzyl ester

Conditions
ConditionsYield
With Tris-HCl buffer; α-chymotropsin In water; N,N-dimethyl-formamide at 25℃; pH 9;A n/a
B 31%
(R,S)-N-acetyl phenylalanine
2901-75-9

(R,S)-N-acetyl phenylalanine

(1S)-endo-fenchylamine
131348-01-1

(1S)-endo-fenchylamine

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

(R,S)-N-acetyl phenylalanine
2901-75-9

(R,S)-N-acetyl phenylalanine

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

L-tyrosine
60-18-4

L-tyrosine

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
Reaktion ueber mehrere Stufen;
2-methyl-4-benzyl-4H-oxazolin-5-one
5469-44-3

2-methyl-4-benzyl-4H-oxazolin-5-one

A

(R)-N-acetylphenylalanin
10172-89-1

(R)-N-acetylphenylalanin

B

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With alpha cyclodextrin In water; acetonitrile pH 7.86; Title compound not separated from byproducts;
2-(N-acetylamino)cinnamic acid
55065-02-6, 64590-80-3, 5469-45-4

2-(N-acetylamino)cinnamic acid

A

(R)-N-acetylphenylalanin
10172-89-1

(R)-N-acetylphenylalanin

B

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With hydrogen In methanol at 25℃; under 3150.3 Torr; for 4h; Product distribution; enantioselectivity of reaction dependent on various rhodium complexes with 1,2-bis(phosphanyl)pyrrolidine ligands; various conditions; also N-acetylcinnamic acid methylester;
With 2S-MeN(PPh2)CHC7H7CH2OPPh2; hydrogen; Rh<(COD)Cl>2 Product distribution; other reagents;
With hydrogen; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; Br>n In ethanol at 20℃; Product distribution; asymmetric catalytic hydrogenation, enantiodifferentiating ability of the catalysts: atmospheric pressure of H2; var. catalysts, pressure, temp. and initial rate;
ethyl N-acetyl-DL-phenylalaninate
4134-09-2

ethyl N-acetyl-DL-phenylalaninate

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
In water α-chymotrypsin, 0.05 M phosphate buffer pH 7.4;
(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

(S)-2-acetylamino-3-cyclohexylpropionic acid
100400-96-2, 97290-54-5

(S)-2-acetylamino-3-cyclohexylpropionic acid

Conditions
ConditionsYield
With platinum(IV) oxide; hydrogen; acetic acid In methanol under 2585.81 Torr; for 24h;100%
With hydrogen; rhodium on alumina In methanol for 56h; Ambient temperature; Pressure (range begins): 2.5 ;98.1%
With C33H49ClNRh; hydrogen In 2,2,2-trifluoroethanol at 20℃; under 45004.5 Torr; for 24h; Autoclave; Molecular sieve;93%
With acetic acid; platinum Hydrogenation;
With sodium tetrahydroborate; rhodium(III) chloride 30 deg C, water, pH=4; Yield given. Multistep reaction;
2-hydroxy-1,1,2-trimethylpropyl ethylcarbamate
743477-27-2

2-hydroxy-1,1,2-trimethylpropyl ethylcarbamate

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

A

4,4,5,5-tetramethyl-1,3-dioxolan-2-one
19424-29-4

4,4,5,5-tetramethyl-1,3-dioxolan-2-one

B

ethyl N-acetyl-(L)-phenylalaninate
2361-96-8

ethyl N-acetyl-(L)-phenylalaninate

Conditions
ConditionsYield
With tert.-butylnitrite; 3 A molecular sieve In dichloromethane at 60℃; for 12h;A n/a
B 100%
(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

ethyl-(2-hydroxy-ethyl)-dimethyl-ammonium; hydroxide
76290-84-1

ethyl-(2-hydroxy-ethyl)-dimethyl-ammonium; hydroxide

C6H16NO(1+)*C11H12NO3(1-)

C6H16NO(1+)*C11H12NO3(1-)

Conditions
ConditionsYield
In water at 20℃;100%
(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

C7H18NO(1+)*HO(1-)

C7H18NO(1+)*HO(1-)

C11H12NO3(1-)*C7H18NO(1+)

C11H12NO3(1-)*C7H18NO(1+)

Conditions
ConditionsYield
In water at 20℃;100%
(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

butyl(2-hydroxyethyl)dimethylammonium hydroxide
114380-13-1

butyl(2-hydroxyethyl)dimethylammonium hydroxide

C11H12NO3(1-)*C8H20NO(1+)

C11H12NO3(1-)*C8H20NO(1+)

Conditions
ConditionsYield
In water at 20℃;100%
(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

C9H22NO(1+)*HO(1-)

C9H22NO(1+)*HO(1-)

C11H12NO3(1-)*C9H22NO(1+)

C11H12NO3(1-)*C9H22NO(1+)

Conditions
ConditionsYield
In water at 20℃;100%
(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

ethyl iodide
75-03-6

ethyl iodide

ethyl N-acetyl-(L)-phenylalaninate
2361-96-8

ethyl N-acetyl-(L)-phenylalaninate

Conditions
ConditionsYield
With caesium carbonate In acetonitrile for 1.5h; Heating;99%
With cesium fluoride In N,N-dimethyl-formamide at 15℃; for 24h;90%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

N-acetyl-L-phenylalanine N-hydroxysuccinimide ester
55604-95-0

N-acetyl-L-phenylalanine N-hydroxysuccinimide ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 3.5h;99%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃;85%
With dicyclohexyl-carbodiimide at 0 - 20℃;
(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

L-phenylalanine tert-butyl ester hydrochloride
15100-75-1

L-phenylalanine tert-butyl ester hydrochloride

N-Acetylphenylalanylphenylalanine tert-butyl ester
128992-42-7

N-Acetylphenylalanylphenylalanine tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 23h;99%
(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

(S)-2-acetylamino-3-cyclohexylpropionic acid
100400-96-2, 97290-54-5

(S)-2-acetylamino-3-cyclohexylpropionic acid

Conditions
ConditionsYield
In methanol98.1%
(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

L-phenylalanine
63-91-2

L-phenylalanine

Conditions
ConditionsYield
With pepsin immobilized on terephthalaldehyde functionalized chitosan magnetic nanoparticle In acetonitrile at 20℃; for 48h; pH=2;98%
With hydrogenchloride
With hydrogen bromide
2-iodo-propane
75-30-9

2-iodo-propane

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

isopropyl α-acetylamido-3-phenylpropanoate

isopropyl α-acetylamido-3-phenylpropanoate

Conditions
ConditionsYield
With caesium carbonate In acetonitrile for 1.5h; Heating;98%
(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

(R)-mandelic acid ethyl ester
10606-72-1

(R)-mandelic acid ethyl ester

(R)-2-Acetylamino-3-phenyl-propionic acid (S)-ethoxycarbonyl-phenyl-methyl ester

(R)-2-Acetylamino-3-phenyl-propionic acid (S)-ethoxycarbonyl-phenyl-methyl ester

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 6h; Mitsunobu reaction;98%
1,1,1,3',3',3'-hexafluoro-propanol
920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

C14H13F6NO3

C14H13F6NO3

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 4.5h;96%
methanol
67-56-1

methanol

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

(S)-N-acetylphenylalanine
3618-96-0

(S)-N-acetylphenylalanine

Conditions
ConditionsYield
With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride95%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 70℃; for 20h;95%
With N-Bromosuccinimide at 70℃; for 20h;91%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

N-acetyl-L-phenylalanyl-L-phenylalanine methylester
2562-48-3

N-acetyl-L-phenylalanyl-L-phenylalanine methylester

Conditions
ConditionsYield
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride95%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 12h;53%
With sodium hydroxide; thermolysin at 37℃; for 24h; pH=6.3; enzymatic amidation;
(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

2-amino-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionic acid ethyl ester
849770-98-5

2-amino-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionic acid ethyl ester

(R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionic acid ethyl ester

(R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionic acid ethyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate95%
(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

silver(l) oxide
20667-12-3

silver(l) oxide

[Ag((S)-N-acetylphenylalanate)]

[Ag((S)-N-acetylphenylalanate)]

Conditions
ConditionsYield
In acetonitrile slurry (S)-N-acetylphenylalanine in MeCN was added to slid Ag2O and stirred for 24 h in the dark; ppt. was filtered off, washed with Et2O, and dried in vacuo; elem. anal.;95%
(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

2,4,6-trivinylcyclotriboroxane*pyridine complex

2,4,6-trivinylcyclotriboroxane*pyridine complex

(L)-N-acetyl-phenylalanine vinyl ester
147092-06-6

(L)-N-acetyl-phenylalanine vinyl ester

Conditions
ConditionsYield
With N,N'-diethylurea; copper(II) bis(trifluoromethanesulfonate); triethylamine In tetrahydrofuran at 50℃; for 16h; Chan-Lam Coupling;94%
(S)-2-acetylamino-3-phenylpropanoic acid
2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

chloroacetonitrile
107-14-2

chloroacetonitrile

(S)-cyanomethyl 2-acetamido-3-phenylpropanoate
61781-58-6

(S)-cyanomethyl 2-acetamido-3-phenylpropanoate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 0 - 20℃; for 4.5h;93%
With N-ethyl-N,N-diisopropylamine for 12h;90%
With N-ethyl-N,N-diisopropylamine for 12h;90%
With triethylamine In acetonitrile at 20℃; for 16h; Inert atmosphere;89%
With triethylamine

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