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10569-72-9

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10569-72-9 Usage

Uses

DL-3-Aminoisobutyric Acid is a useful compound for suppressing atherosclerosis in apolipoprotein E-knockout mouse.

Purification Methods

RS-β-Aminoisobutyric acid forms colourless prisms by crystallisation from hot H2O which are powdered and dried in vacuo. The purity is checked by paper chromatography (Whatman 1) using ninhydrin spray to visualise the amino acid; RF values in 95% MeOH and n-PrOH/5N HCOOH (8:2) are 0.36 and 0.50 respectively. [Kupiecki & Coon Biochemical Preparations 7 20 1960, Pollack J Am Chem Soc 65 1335 1943.] The R-enantiomer, isolated from iris bulbs or human urine, crystallises from H2O and sublimes in vacuo [Asen et al. J Biol Chem 234 343 1959]. The RS-hydrochloride crystallises from EtOH/Et2O with m 128-129o (also 130o) [B.hme et al. Chem Ber 92 1258, 1260, 1261 1959]. [Beilstein 4 III 1330.]

Check Digit Verification of cas no

The CAS Registry Mumber 10569-72-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,5,6 and 9 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 10569-72:
(7*1)+(6*0)+(5*5)+(4*6)+(3*9)+(2*7)+(1*2)=99
99 % 10 = 9
So 10569-72-9 is a valid CAS Registry Number.
InChI:InChI=1/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)

10569-72-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-aminoisobutyric acid

1.2 Other means of identification

Product number -
Other names AIB

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:10569-72-9 SDS

10569-72-9Synthetic route

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With phosphoric acid; dihydropyrimidinase; N-carbamoyl- -alanine amidohydrolase; nickel dichloride In aq. phosphate buffer at 30℃; pH=8; Enzymatic reaction;
2-benzyl-4-methylisoxazolidin-5-one
95503-63-2

2-benzyl-4-methylisoxazolidin-5-one

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In 1,4-dioxane; water at 85℃; for 16h;95%
4-methyl-N-(S)-1-phenylethylisoxazolidin-5-one
95503-68-7, 95503-69-8

4-methyl-N-(S)-1-phenylethylisoxazolidin-5-one

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In 1,4-dioxane; water at 85℃; for 16h;87%
trans-1-benzoyl-2-tert-butyl-3,5-dimethylperhydropyrimidin-4-one
131932-58-6

trans-1-benzoyl-2-tert-butyl-3,5-dimethylperhydropyrimidin-4-one

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With hydrogenchloride at 180℃; for 8h;69%
2-methyl-3-benzylaminopropanoic acid
66839-25-6

2-methyl-3-benzylaminopropanoic acid

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol
With hydrogen; PdCl2/C In acetic acid
2-dibenzylaminomethyl-propionic acid

2-dibenzylaminomethyl-propionic acid

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In tetrahydrofuran; methanol
(2S,3S)-3-Methyl-1-(toluene-4-sulfonyl)-azetidine-2-carboxylic acid

(2S,3S)-3-Methyl-1-(toluene-4-sulfonyl)-azetidine-2-carboxylic acid

A

(2S,3S)-3-methylazetidine-2-carboxylic acid

(2S,3S)-3-methylazetidine-2-carboxylic acid

B

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With naphthalene; sodium In 1,2-dimethoxyethane at -78℃; for 0.5h;A 31 mg
B n/a
(2R,3R)-3-Methyl-1-(toluene-4-sulfonyl)-azetidine-2-carboxylic acid

(2R,3R)-3-Methyl-1-(toluene-4-sulfonyl)-azetidine-2-carboxylic acid

A

(2R,3R)-3-methylazetidine-2-carboxylic acid

(2R,3R)-3-methylazetidine-2-carboxylic acid

B

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With naphthalene; sodium In 1,2-dimethoxyethane at -78℃; for 0.5h;A 67 mg
B n/a
ethyl 2-cyanopropionate
1572-99-2

ethyl 2-cyanopropionate

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With sulfuric acid; acetic acid; platinum Hydrogenation.wiederholtes Eindampfen des Reaktionsprodukts mit Wasser;
N,N,O-Tris-(trimethylsilyl)-β-aminoisobuttersaeure
55125-15-0

N,N,O-Tris-(trimethylsilyl)-β-aminoisobuttersaeure

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With water; triethylamine In tetrahydrofuran; pentane at 20℃;
methyl methacrylate
97-63-2

methyl methacrylate

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With ethanol; ammonia; water; hydroquinone at 125 - 130℃; und Erwaermen des Reaktionsprodukts mit wss.HCl;
β-amino-α-methyl propionic acid methyl ester
14678-48-9

β-amino-α-methyl propionic acid methyl ester

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With lithium hydroxide In water
YM-170320

YM-170320

A

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

B

α-aminoacrylic acid
1948-56-7

α-aminoacrylic acid

C

2-amino-4-hydroxypentanedioic acid
32909-71-0

2-amino-4-hydroxypentanedioic acid

Conditions
ConditionsYield
With hydrogenchloride at 110℃; for 17h; Hydrolysis;
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With Canyon Diablo iron meteorites at 140℃; for 24h; Reagent/catalyst; Temperature;
methacrylonitrile
126-98-7

methacrylonitrile

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With sulfuric acid; sulfur trioxide
propylamine
107-10-8

propylamine

formic acid
64-18-6

formic acid

A

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

B

rac-Ala-OH
302-72-7

rac-Ala-OH

C

2-aminobutanoic acid
2835-81-6

2-aminobutanoic acid

D

4-amino-n-butyric acid
56-12-2

4-amino-n-butyric acid

Conditions
ConditionsYield
In water at 10 - 20℃; for 1h; contact glow discharge electrolysis (500-600 V, 45 mA); Further byproducts given;A 9.8%
B 3.4%
C 0.9%
D 8.1%
propylamine
107-10-8

propylamine

formic acid
64-18-6

formic acid

A

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

B

2-aminobutanoic acid
2835-81-6

2-aminobutanoic acid

C

3-amino propanoic acid
107-95-9

3-amino propanoic acid

D

4-amino-n-butyric acid
56-12-2

4-amino-n-butyric acid

Conditions
ConditionsYield
In water at 10 - 20℃; for 1h; contact glow discharge electrolysis (500-600 V, 45 mA); Further byproducts given;A 9.8%
B 0.9%
C 3.4%
D 8.1%
Sodium; 2-methyl-3-ureido-propionate
84796-57-6

Sodium; 2-methyl-3-ureido-propionate

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With hydrogen cation Yield given;
(+-)-β-phthalimido-isobutyric acid anilide

(+-)-β-phthalimido-isobutyric acid anilide

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With hydrogen iodide; acetic acid
β-amino-isobutyric acid ethyl ester hydrochloride

β-amino-isobutyric acid ethyl ester hydrochloride

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With water wiederholtes Eindampfen;
(benzoylamino-methyl)-methyl-malonic acid diethyl ester
102076-62-0

(benzoylamino-methyl)-methyl-malonic acid diethyl ester

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
With hydrogen bromide
methacrylic acid methyl ester
80-62-6

methacrylic acid methyl ester

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
(i) NH3, MeOH, (ii) aq. HCl; Multistep reaction;
formic acid
64-18-6

formic acid

1-amino-2-propene
107-11-9

1-amino-2-propene

A

propylamine
107-10-8

propylamine

B

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

C

glycine
56-40-6

glycine

D

3-amino propanoic acid
107-95-9

3-amino propanoic acid

E

4-amino-n-butyric acid
56-12-2

4-amino-n-butyric acid

Conditions
ConditionsYield
With hydrogen; oxygen In water for 3h; Product distribution; various unsaturated amines; investigation of the direct carboxylation of C=C bond, the effect of formic acid concentration as well as the flame composition on product(s); radical mechanism is proposed;A n/a
B 38%
C n/a
D n/a
E 5%
2-cyanopropanoic acid
632-07-5

2-cyanopropanoic acid

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
Hydrogenation;
sulfuric acid
7664-93-9

sulfuric acid

ethyl 2-cyanopropionate
1572-99-2

ethyl 2-cyanopropionate

acetic acid
64-19-7

acetic acid

PtO2

PtO2

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Conditions
ConditionsYield
beim folgenden Verseifen.Hydrogenation;
propylamine
107-10-8

propylamine

formic acid
64-18-6

formic acid

A

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

B

glycine
56-40-6

glycine

C

2-aminobutanoic acid
2835-81-6

2-aminobutanoic acid

D

3-amino propanoic acid
107-95-9

3-amino propanoic acid

E

4-amino-n-butyric acid
56-12-2

4-amino-n-butyric acid

Conditions
ConditionsYield
In water at 10 - 20℃; for 1h; Product distribution; contact glow discharge electrolysis; variation of pH, effect of time;A 9.8%
B 0.2%
C 0.9%
D 3.4%
E 8.1%
isobutyric Acid
79-31-2

isobutyric Acid

A

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

B

2-Aminoisobutyric acid
62-57-7

2-Aminoisobutyric acid

Conditions
ConditionsYield
With hydrogen azide for 5h; Quantum yield; Ambient temperature; Irradiation;
ethanol
64-17-5

ethanol

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

ethyl 3-amino-2-methylpropanoate
22560-81-2

ethyl 3-amino-2-methylpropanoate

Conditions
ConditionsYield
With hydrogenchloride100%
With thionyl chloride for 4.5h;85%
Stage #1: ethanol; DL-3-aminoisobutyric acid With thionyl chloride at 0 - 90℃; for 6h;
Stage #2: With ammonium hydroxide In dichloromethane at 20℃; for 2h;
methanol
67-56-1

methanol

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

β-amino-α-methyl propionic acid methyl ester
14678-48-9

β-amino-α-methyl propionic acid methyl ester

Conditions
ConditionsYield
With thionyl chloride at 20℃;100%
With thionyl chloride for 3h; Reflux;
With thionyl chloride at 0 - 20℃;
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

3-amino-2-methylpropan-1-ol hydrochloride
66164-10-1

3-amino-2-methylpropan-1-ol hydrochloride

Conditions
ConditionsYield
Stage #1: DL-3-aminoisobutyric acid With borane-THF In tetrahydrofuran at 20℃; for 20.5h; Reflux;
Stage #2: With hydrogenchloride In 1,4-dioxane; diethyl ether for 0.333333h;
100%
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-tert-butoxycarbonyl-3-amino-2(RS)-methylpropionic acid
16948-10-0

N-tert-butoxycarbonyl-3-amino-2(RS)-methylpropionic acid

Conditions
ConditionsYield
With sodium hydroxide; tert-butyl alcohol In water at 30℃; for 18h;99%
With sodium hydroxide In tetrahydrofuran at 20 - 30℃; for 18h;97%
Stage #1: DL-3-aminoisobutyric acid; di-tert-butyl dicarbonate With sodium hydroxide In 1,4-dioxane; water at 5℃; for 0.916667h;
Stage #2: With hydrogenchloride In 1,4-dioxane; water
96%
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

1-chloro-2,6-dinitrobenzene
606-21-3

1-chloro-2,6-dinitrobenzene

3-(2,6-Dinitro-phenylamino)-2-methyl-propionic acid
189939-44-4

3-(2,6-Dinitro-phenylamino)-2-methyl-propionic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol for 6h; Heating;98%
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

3,5-dichlorobenzoyl chloride
2905-62-6

3,5-dichlorobenzoyl chloride

3-(3,5-dichlorobenzamido)-2-methylpropanoic acid

3-(3,5-dichlorobenzamido)-2-methylpropanoic acid

Conditions
ConditionsYield
With sodium hydroxide In water for 1h;93%
methanol
67-56-1

methanol

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

β-aminoisobutyric acid methyl ester hydrochloride
88512-06-5

β-aminoisobutyric acid methyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃; for 6h;90%
With trimethylsilyl isocyanate at 0 - 20℃; for 48h; Inert atmosphere;75%
With thionyl chloride at -10℃; for 1h; Heating / reflux;
With thionyl chloride at 0℃; for 18h; Inert atmosphere; Reflux;
formaldehyd
50-00-0

formaldehyd

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Isochroman-3-carboxylic acid methyl ester

Isochroman-3-carboxylic acid methyl ester

Conditions
ConditionsYield
Stage #1: formaldehyd; DL-3-aminoisobutyric acid With trifluoroacetic acid at 150℃; for 0.0833333h; Sealed tube; Inert atmosphere; Microwave irradiation;
Stage #2: With sulfuric acid In methanol for 4h; Reflux;
90%
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

(1S)-(-)-camphanic chloride
39637-74-6

(1S)-(-)-camphanic chloride

(2RS)-3-camphanoylamino-2-methylpropanoic acid
88099-59-6, 88099-60-9, 98974-77-7

(2RS)-3-camphanoylamino-2-methylpropanoic acid

Conditions
ConditionsYield
With sodium hydroxide In water; toluene for 3h;89%
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

3-methyl-2-azetidinone
58521-61-2

3-methyl-2-azetidinone

Conditions
ConditionsYield
With sulfenamide (5); triphenylphosphine In acetonitrile at 80℃; for 2h;89%
With tris(2-oxo-3-oxazolinyl)phosphine oxide; triethylamine In acetonitrile for 6h; Heating;75%
With tris(1,3-dihydro-2-oxobenzoxazolin-3-yl) phosphine oxide; triethylamine In acetonitrile for 6h; Heating;71%
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In acetonitrile for 2h; Heating;57%
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

phenylacetaldehyde
122-78-1

phenylacetaldehyde

N-tert-butyl-2-(3-methyl-2-oxoazetidin-1-yl)-3-phenylpropanamide

N-tert-butyl-2-(3-methyl-2-oxoazetidin-1-yl)-3-phenylpropanamide

Conditions
ConditionsYield
Stage #1: DL-3-aminoisobutyric acid; phenylacetaldehyde In water at 20℃;
Stage #2: tert-butylisonitrile In water at 20℃; Ugi reaction;
88%
In methanol for 24h; Ambient temperature;
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Benzyl isocyanide
88333-03-3, 10340-91-7

Benzyl isocyanide

propionaldehyde
123-38-6

propionaldehyde

N-benzyl-2-(3-methyl-2-oxoazetidin-1-yl)butanamide

N-benzyl-2-(3-methyl-2-oxoazetidin-1-yl)butanamide

Conditions
ConditionsYield
Stage #1: DL-3-aminoisobutyric acid; propionaldehyde In water at 20℃;
Stage #2: Benzyl isocyanide In water at 20℃; Ugi reaction;
84%
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

isobutyraldehyde
78-84-2

isobutyraldehyde

N-tert-butyl-3-methyl-2-(3-methyl-2-oxoazetidin-1-yl)butanamide

N-tert-butyl-3-methyl-2-(3-methyl-2-oxoazetidin-1-yl)butanamide

Conditions
ConditionsYield
Stage #1: DL-3-aminoisobutyric acid; isobutyraldehyde In water at 20℃;
Stage #2: tert-butylisonitrile In water at 20℃; Ugi reaction;
82%
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Benzyl isocyanide
88333-03-3, 10340-91-7

Benzyl isocyanide

isobutyraldehyde
78-84-2

isobutyraldehyde

N-benzyl-3-methyl-2-(3-methyl-2-oxoazetidin-1-yl)butanamide

N-benzyl-3-methyl-2-(3-methyl-2-oxoazetidin-1-yl)butanamide

Conditions
ConditionsYield
Stage #1: DL-3-aminoisobutyric acid; isobutyraldehyde In water at 20℃;
Stage #2: Benzyl isocyanide In water at 20℃; Ugi reaction;
82%
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

Benzyl isocyanide
88333-03-3, 10340-91-7

Benzyl isocyanide

isovaleraldehyde
590-86-3

isovaleraldehyde

N-benzyl-4-methyl-2-(3-methyl-2-oxoazetidin-1-yl)pentanamide

N-benzyl-4-methyl-2-(3-methyl-2-oxoazetidin-1-yl)pentanamide

Conditions
ConditionsYield
Stage #1: DL-3-aminoisobutyric acid; isovaleraldehyde In water at 20℃;
Stage #2: Benzyl isocyanide In water at 20℃; Ugi reaction;
82%
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

isovaleraldehyde
590-86-3

isovaleraldehyde

N-tert-butyl-4-methyl-2-(3-methyl-2-oxoazetidin-1-yl)pentanamide

N-tert-butyl-4-methyl-2-(3-methyl-2-oxoazetidin-1-yl)pentanamide

Conditions
ConditionsYield
Stage #1: DL-3-aminoisobutyric acid; isovaleraldehyde In water at 20℃;
Stage #2: tert-butylisonitrile In water at 20℃; Ugi reaction;
81%
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

2-methoxy-5-methylphenyl isocyanate
59741-04-7

2-methoxy-5-methylphenyl isocyanate

3-(3-(2-methoxy-5-methylphenyl)ureido)-2-methylpropanoic acid
1270915-86-0

3-(3-(2-methoxy-5-methylphenyl)ureido)-2-methylpropanoic acid

Conditions
ConditionsYield
In methanol at 20℃;81%
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

2-methyl-3-(2,2,2-trifluoroacetamido)propanoic acid
101642-73-3

2-methyl-3-(2,2,2-trifluoroacetamido)propanoic acid

Conditions
ConditionsYield
Stage #1: DL-3-aminoisobutyric acid With triethylamine In methanol for 0.0833333h;
Stage #2: ethyl trifluoroacetate, In methanol for 24h;
81%
methanol
67-56-1

methanol

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

[di(propan-2-yl)amino](oxo)acetyl chloride
141109-47-9

[di(propan-2-yl)amino](oxo)acetyl chloride

methyl 3-(2-(diisopropylamino)-2-oxoacetamido)-2-methylpropanoate

methyl 3-(2-(diisopropylamino)-2-oxoacetamido)-2-methylpropanoate

Conditions
ConditionsYield
Stage #1: methanol; DL-3-aminoisobutyric acid With thionyl chloride at 0 - 20℃;
Stage #2: [di(propan-2-yl)amino](oxo)acetyl chloride With triethylamine In dichloromethane at 0 - 20℃; for 6h;
78%
2,5-dimethylphenyl isocyanate
40397-98-6

2,5-dimethylphenyl isocyanate

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

3-(3-(2,5-dimethylphenyl)ureido)-2-methylpropanoic acid
1337962-17-0

3-(3-(2,5-dimethylphenyl)ureido)-2-methylpropanoic acid

Conditions
ConditionsYield
In methanol at 20℃;76%
iodobenzene
591-50-4

iodobenzene

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

N-phenyl-3-aminoisobutyric acid
73849-53-3

N-phenyl-3-aminoisobutyric acid

Conditions
ConditionsYield
With potassium phosphate; copper(I) bromide; 1,1'-bi-2-naphthol In N,N-dimethyl-formamide at 40℃; for 10h;72%
phthalic anhydride
85-44-9

phthalic anhydride

DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

3-(1,3-dioxoisoindolin-2-yl)-2-methylpropanoic acid
24431-49-0

3-(1,3-dioxoisoindolin-2-yl)-2-methylpropanoic acid

Conditions
ConditionsYield
With triethylamine In toluene Reflux;70%
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

3-bromo-1‐(4‐methoxybenzyl)‐4‐nitro-1H‐pyrazole

3-bromo-1‐(4‐methoxybenzyl)‐4‐nitro-1H‐pyrazole

3-((1-(4‐methoxybenzyl)‐4‐nitro‐1H‐pyrazol-3-yl)amino)-2-methylpropanoic acid

3-((1-(4‐methoxybenzyl)‐4‐nitro‐1H‐pyrazol-3-yl)amino)-2-methylpropanoic acid

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate In water; N,N-dimethyl-formamide at 150℃; for 4h; Microwave irradiation;70%
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

2,2,2-Trichloroethyl chloroformate
17341-93-4

2,2,2-Trichloroethyl chloroformate

2-methyl-3-((2,2,2-trichloroethoxy)carbonylamino)propanoic acid
1417602-90-4

2-methyl-3-((2,2,2-trichloroethoxy)carbonylamino)propanoic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 0 - 20℃; for 2.5h;68%
DL-3-aminoisobutyric acid
10569-72-9

DL-3-aminoisobutyric acid

4-chloro-2-isocyanato-1-methylbenzene
40411-27-6

4-chloro-2-isocyanato-1-methylbenzene

3-(3-(5-chloro-2-methylphenyl)ureido)-2-methylpropanoic acid
1337962-18-1

3-(3-(5-chloro-2-methylphenyl)ureido)-2-methylpropanoic acid

Conditions
ConditionsYield
In methanol at 20℃;61%

10569-72-9Relevant articles and documents

A new enantioselective synthesis of β-amino acids

Saylik, Dilek,Campi, Eva M.,Donohue, Andrew C.,Jackson,Robinson, Andrea J.

, p. 657 - 667 (2001)

Enantioselective hydrogenation of some α,β-unsaturated nitriles and their corresponding methyl esters bearing a phthalimidomethyl substituent at the α-carbon using Rh-DuPHOS catalysts afforded β-amino acid precursors with modest e.e.s of up to 48%. Hydrogenation of the α,β-unsaturated methyl esters using a Ru-BINAP catalyst gave higher e.e.s of up to 84%. Method development for the determination of the enantiomeric excesses of these derivatives using chiral HPLC is also reported.

Diastereoselective total synthesis and structural confirmation of surugamide F

Kuranaga, Takefumi,Fukuba, Atsuki,Ninomiya, Akihiro,Takada, Kentaro,Matsunaga, Shigeki,Wakimoto, Toshiyuki

, p. 637 - 641 (2018)

Surugamide F is a linear decapeptide (1) isolated along with the cyclic octapeptides surugamides A–E (2–6), from a marine-derived Streptomyces species. The linear peptide 1 is produced by two nonribosomal peptide synthetases (NRPSs) encoded in adjacent open reading frames, which are further flanked by an additional pair of NRPS genes responsible for the biosyntheses of the cyclic peptides 2–6. While the cyclic peptides 2–6 were identified to be cathepsin B inhibitors, the biological activity of the new metabolite 1 still remained unclear. In order to elucidate its unique biosynthetic pathway and biological activity in detail, we planned to develop an efficient synthetic route toward 1. Here we report the diastereoselective total synthesis of 1, utilizing 9-fluorenylmethyloxycarbonyl (Fmoc)-based solid-phase peptide synthesis. During this study, we found that the structural correction of 1 was required, due to the mislabeling of the commercially obtained 3-amino-2-methylpropionic acid, and the true structure of 1 was corroborated by the chemical synthesis and chromatographic comparison.

New biocatalytic route for the production of enantioenriched β-alanine derivatives starting from 5- and 6-monosubstituted dihydrouracils

Martínez-Gómez, Ana Isabel,Clemente-Jiménez, Josefa María,Rodríguez-Vico, Felipe,Kanerva, Liisa T.,Li, Xiang-Guo,Heras-Vázquez, Francisco Javier Las,Martínez-Rodríguez, Sergio

, p. 2090 - 2096 (2012)

Taking advantage of the catalytic promiscuity of pyrimidine-catabolism enzymes (dihydropyrimidinase (E.C. 3.5.2.2), N-carbamoyl-β-alanine amidohydrolase (E.C. 3.5.1.6)), the production of different β-alanine derivatives starting from 5- and 6-monosubstituted dihydrouracils has been evaluated using a mimesis approach. In this work, the S-enantioselective character of dihydropyrimidinase from Sinorizhobium meliloti toward 6-monosubstituted dihydrouracil derivatives has been shown. An inverted R-/S-enantioselectivity of N-carbamoyl-β-alanine amidohydrolase from Agrobacterium tumefaciens toward two different N-carbamoyl-β-amino acids has been proved. Our results have shown for the first time that this mimetic tandem constitutes an interesting biotechnological tool for the preparation of different β-alanine derivatives in an environmentally friendly way, allowing the production of enantioenriched (R)-α-phenyl-β-alanine (e.e. > 95%) and (R)-α-methyl-β-alanine (e.e. > 90%).

Modular Enzymatic Cascade Synthesis of Vitamin B5 and Its Derivatives

Abidin, Mohammad Z.,Saravanan, Thangavelu,Zhang, Jielin,Tepper, Pieter G.,Strauss, Erick,Poelarends, Gerrit J.

, p. 17434 - 17438 (2018)

Access to vitamin B5 [(R)-pantothenic acid] and both diastereoisomers of α-methyl-substituted vitamin B5 [(R)- and (S)-3-((R)-2,4-dihydroxy-3,3-dimethylbutanamido)-2-methylpropanoic acid] was achieved using a modular three-step biocatalytic cascade involving 3-methylaspartate ammonia lyase (MAL), aspartate-α-decarboxylase (ADC), β-methylaspartate-α-decarboxylase (CrpG) or glutamate decarboxylase (GAD), and pantothenate synthetase (PS) enzymes. Starting from simple non-chiral dicarboxylic acids (either fumaric acid or mesaconic acid), vitamin B5 and both diastereoisomers of α-methyl-substituted vitamin B5, which are valuable precursors for promising antimicrobials against Plasmodium falciparum and multidrug-resistant Staphylococcus aureus, can be generated in good yields (up to 70 %) and excellent enantiopurity (>99 % ee). This newly developed cascade process may be tailored and used for the biocatalytic production of various vitamin B5 derivatives by modifying the pantoyl or β-alanine moiety.

-

Pollack

, p. 1335 (1943)

-

Stereoselective α-alkylation of new chiral auxiliaries: An access to enantiomerically pure α- and α,β-substituted β-amino acids

Agami, Claude,Cheramy, Sandrine,Dechoux, Luc

, p. 1838 - 1840 (1999)

New bicyclic heterocycles 5, which are potentially useful for the enantioselective synthesis of substituted β-amino acids, have been synthesized. A study on the α-alkylation of these chiral auxiliaries is presented. An optically pure β-amino acid was obtained in excellent yield from its masked chiral derivative 6a.

The Formation of Amino Acids by the Reactions of Singlet NH with Several Carboxylic Acids

Tsunashima, Shigeru,Kitamura, Takashi,Sato, Shin

, p. 2869 - 2871 (1981)

The photolysis of hydrogen azide was studied in liquid acetic acid, propionic acid, and isobutyric acid at room temperature.The formation of amino acids was confirmed by the color reactions with ninhydrin and with chromotropic acid and by the NMR spectra.From the propionic acid, α- and β-alanine were formed in the ratio of 1.5.In the case of isobutyric acid, α- and β-aminoisobutyric acids were formed in the ratio of about 5.These results are explained by the insertion reaction of NH(a1Δ) into the C-H bonds of carboxylic acids.

Catalytic Asymmetric Synthesis of Unprotected β2-Amino Acids

Zhu, Chendan,Mandrelli, Francesca,Zhou, Hui,Maji, Rajat,List, Benjamin

supporting information, p. 3312 - 3317 (2021/04/07)

We report here a scalable, catalytic one-pot approach to enantiopure and unmodified β2-amino acids. A newly developed confined imidodiphosphorimidate (IDPi) catalyzes a broadly applicable reaction of diverse bis-silyl ketene acetals with a silylated aminomethyl ether, followed by hydrolytic workup, to give free β2-amino acids in high yields, purity, and enantioselectivity. Importantly, both aromatic and aliphatic β2-amino acids can be obtained using this method. Mechanistic studies are consistent with the aminomethylation to proceed via silylium-based asymmetric counteranion-directed catalysis (Si-ACDC) and a transition state to explain the enantioselectivity is suggested on the basis of density functional theory calculation.

β2-Homo-amino acid scan of μ-selective opioid tetrapeptide TAPP

Kosson, Piotr,Lipiński, Piotr F. J.,Misicka, Aleksandra,Tymecka, Dagmara

, (2020/08/11)

TAPP (H-Tyr-d-Ala-Phe-Phe-NH2) is a potent, μ-selective opioid ligand. In order to gain further insights into pharmacophoric features of this tetrapeptide, we have performed a β2-Homo-amino acid (β2hAA) scan of the TAPP sequence. To this aim, 10 novel analogues have been synthesized and evaluated for μ-opioid and δ-opioid receptor affinity as well as for stability in human plasma. The derivatives included compounds in which a (R)- or (S)-β2-Homo-Homologue replaced the amino acids in the TAPP sequence. The derivatives with (R)- or (S)-β2hPhe4 turned out to bind μOR with affinities equal to that of the parent. β2hAAs in position 1 and 3 resulted in rather large affinity decreases, but the change differed depending on the stereochemistry. β2-Homologation in the second position gave derivatives with very poor μOR binding. According to molecular modelling, the presented α/β-peptides adopt a variety of binding poses with their common element being an ionic interaction between a protonable amine of the first residue and Asp147. A feature required for high μOR affinity seems the ability to accommodate the ring in the fourth residue in a manner similar to that found for TAPP. Contrary to what might be expected, several compounds were significantly less stable in human plasma than the parent compound.

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