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759-05-7

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759-05-7 Usage

Definition

ChEBI: A 2-oxo monocarboxylic acid that is the 2-oxo derivative of isovaleric acid.

Synthesis Reference(s)

The Journal of Organic Chemistry, 28, p. 3088, 1963Tetrahedron Letters, 19, p. 4809, 1978 DOI: 10.1016/S0040-4039(01)85738-5

Check Digit Verification of cas no

The CAS Registry Mumber 759-05-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,5 and 9 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 759-05:
(5*7)+(4*5)+(3*9)+(2*0)+(1*5)=87
87 % 10 = 7
So 759-05-7 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)

759-05-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-methyl-2-oxobutanoic acid

1.2 Other means of identification

Product number -
Other names Butanoic acid, 3-methyl-2-oxo-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:759-05-7 SDS

759-05-7Synthetic route

ethyl 3-methyl-2-oxobutanoate
20201-24-5

ethyl 3-methyl-2-oxobutanoate

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With water; lithium hydroxide at 0 - 25℃; for 1h; Inert atmosphere;95%
With sodium hydroxide In water at 0 - 23℃; for 0.666667h;62%
With potassium hydroxide
4-isopropylidene-oxazolidine-2,5-dione
7682-64-6

4-isopropylidene-oxazolidine-2,5-dione

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran for 0.5h; Ambient temperature;95%
2,5-dihydro-4-(1-methylethyl)-2-(3-oxocyclohexyl)-oxazol-5-one
152343-06-1

2,5-dihydro-4-(1-methylethyl)-2-(3-oxocyclohexyl)-oxazol-5-one

A

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

B

3-oxocyclohexanecarbaldehyde
69814-26-2

3-oxocyclohexanecarbaldehyde

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran Ambient temperature;A n/a
B 84%
methyl 2,5-dihydro-4-(1-methylethyl)-γ,5-dioxo-2-oxazol-undecanoate
152343-05-0

methyl 2,5-dihydro-4-(1-methylethyl)-γ,5-dioxo-2-oxazol-undecanoate

A

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

B

11-formyl-9-oxo-undecanoic acid methyl ester
50266-44-9

11-formyl-9-oxo-undecanoic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran Ambient temperature;A n/a
B 80%
2,5-dihydro-4-(1-methylethyl)-5-oxo-2-(3-oxobutyl)-oxazol-5-one
152343-03-8

2,5-dihydro-4-(1-methylethyl)-5-oxo-2-(3-oxobutyl)-oxazol-5-one

A

4-oxopentanal
626-96-0

4-oxopentanal

B

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran Ambient temperature;A 76%
B n/a
methyl 2,5-dihydro-4-(1-methylethyl)-5-oxo-2-oxazol-propionate
152343-04-9

methyl 2,5-dihydro-4-(1-methylethyl)-5-oxo-2-oxazol-propionate

A

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

B

4-oxobutanoic acid methyl ester
13865-19-5

4-oxobutanoic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran Ambient temperature;A n/a
B 72%
2,5-dihydro-4-(1-methylethyl)-2-(3-oxocyclopentyl)-oxazol-5-one
152343-07-2

2,5-dihydro-4-(1-methylethyl)-2-(3-oxocyclopentyl)-oxazol-5-one

A

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

B

3-formylcyclopentanone
77852-95-0, 65550-06-3

3-formylcyclopentanone

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran Ambient temperature;A n/a
B 70%
2-trifluoromethyl-4-isopropyl-Δ3-oxazolin-5-one
2357-39-3

2-trifluoromethyl-4-isopropyl-Δ3-oxazolin-5-one

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With water; sodium hydroxide at 20℃; for 12h; Inert atmosphere;69%
2,5-dihydro-4-(1-methylethyl)-2-(2-nitroethyl)-oxazol-5-one
152343-08-3

2,5-dihydro-4-(1-methylethyl)-2-(2-nitroethyl)-oxazol-5-one

A

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

B

3-nitropropanaldehyde
58657-26-4

3-nitropropanaldehyde

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran Ambient temperature;A n/a
B 64%
2-[((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-4-isopropyl-2H-oxazol-5-one

2-[((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-4-isopropyl-2H-oxazol-5-one

A

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

B

D-erythrose
583-50-6

D-erythrose

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran Ambient temperature;A n/a
B 59%
2,5-dihydro-4-(1-methylethyl)-5-oxo-2-(α-phenyl)-oxazolemethanol

2,5-dihydro-4-(1-methylethyl)-5-oxo-2-(α-phenyl)-oxazolemethanol

A

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

B

(2-Oxo-1-phenyl-ethoxy)-phenyl-acetaldehyde

(2-Oxo-1-phenyl-ethoxy)-phenyl-acetaldehyde

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran Ambient temperature;A n/a
B 51%
2-[Hydroxy-((S)-2-phenyl-[1,3]dioxan-4-yl)-methyl]-4-isopropyl-2H-oxazol-5-one

2-[Hydroxy-((S)-2-phenyl-[1,3]dioxan-4-yl)-methyl]-4-isopropyl-2H-oxazol-5-one

A

L-erythro-4-deoxy-pentose
18439-27-5

L-erythro-4-deoxy-pentose

B

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran Ambient temperature;A 49%
B n/a
2,5-dihydro-2-(1-hydroxyethyl)-4-(1-methylethyl)-oxazol-5-one

2,5-dihydro-2-(1-hydroxyethyl)-4-(1-methylethyl)-oxazol-5-one

A

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

B

2-(1-Methyl-2-oxo-ethoxy)-propionaldehyde

2-(1-Methyl-2-oxo-ethoxy)-propionaldehyde

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran Ambient temperature;A n/a
B 44%
2,5-dihydro-4-(1-methylethyl)-5-oxo-2-oxazol-propionic aldehyde

2,5-dihydro-4-(1-methylethyl)-5-oxo-2-oxazol-propionic aldehyde

A

butanedial
638-37-9

butanedial

B

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran Ambient temperature;A 38%
B n/a
2,5-dihydro-4-(1-methylethyl)-5-oxo-2-<α-(2-nitrophenyl)>-oxazolemethanol

2,5-dihydro-4-(1-methylethyl)-5-oxo-2-<α-(2-nitrophenyl)>-oxazolemethanol

A

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

B

(2-Nitro-phenyl)-[1-(2-nitro-phenyl)-2-oxo-ethoxy]-acetaldehyde

(2-Nitro-phenyl)-[1-(2-nitro-phenyl)-2-oxo-ethoxy]-acetaldehyde

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran Ambient temperature;A n/a
B 37%
pyridine
110-86-1

pyridine

tetrachloromethane
56-23-5

tetrachloromethane

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

2-hydroxy-3-methylbutanenitrile
15344-34-0

2-hydroxy-3-methylbutanenitrile

A

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

B

isobutyraldehyde
78-84-2

isobutyraldehyde

tetrachloromethane
56-23-5

tetrachloromethane

2-bromo-3-methyl-crotonic acid
1578-14-9

2-bromo-3-methyl-crotonic acid

A

(E)-4-hydroxy-3-methylbut-2-enoic acid
44647-19-0

(E)-4-hydroxy-3-methylbut-2-enoic acid

B

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

C

2-hydroxy-3-methylbut-3-enoic acid
91496-47-8

2-hydroxy-3-methylbut-3-enoic acid

Conditions
ConditionsYield
at 100℃;
tetrachloromethane
56-23-5

tetrachloromethane

2-hydroxy-3-methylbut-3-enoic acid
91496-47-8

2-hydroxy-3-methylbut-3-enoic acid

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

5-methyl-3-hexene-2-one
5166-53-0

5-methyl-3-hexene-2-one

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With potassium permanganate
With permanganate(VII) ion Oxydation;
L-valine
72-18-4

L-valine

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With sodium hydroxide; potassium hexacyanoferrate(III) In water at 55℃; Rate constant; Kinetics; Mechanism; var. reagents conc.;
With potassium nitrososulfonate In various solvent(s) at 26.9℃; Thermodynamic data; Rate constant; ΔH (activ.), ΔS (activ.);
With kidneys-extracts
D,L-valine
516-06-3

D,L-valine

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With kidneys-extracts
With perchloric acid; hexachloroiridate(IV) at 34.9℃; Rate constant; Kinetics; Thermodynamic data; var. temp.; ΔH(excit.), ΔG(excit.), ΔS(excit.);
With pyridine-4-carbaldehyde; hydrogenchloride; 1,8-diazabicyclo[5.4.0]undec-7-ene 1.) DMF, r.t., 5 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: (heating)
2: aq. NaOH
View Scheme
With ω-transaminase
2-hydroxy-3-methylbutanoic acid
4026-18-0, 17407-55-5, 17407-56-6, 600-37-3

2-hydroxy-3-methylbutanoic acid

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With Fructose 1,6-bisphosphate; Bacillus stearothermophilus; triethanolamine hydrochloride; NADH at 25℃; Rate constant; Equilibrium constant; also in presence of Gln102 or Asn enzyme;
With potassium hydroxide; potassium permanganate at 20℃;
isobutyryl cyanide
42867-39-0

isobutyryl cyanide

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With hydrogenchloride
2,5-Dimethyl-4-hexen-3-ol
60703-31-3

2,5-Dimethyl-4-hexen-3-ol

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With potassium permanganate
α-chloro β-dimethyl acrylic acid
15052-93-4

α-chloro β-dimethyl acrylic acid

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With sodium hydroxide
2-bromo-3-methyl-crotonic acid
1578-14-9

2-bromo-3-methyl-crotonic acid

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With sodium hydroxide
2-isopropyl-5-methyl-hex-2-enal
35158-25-9

2-isopropyl-5-methyl-hex-2-enal

A

3-methylbutyric acid
503-74-2

3-methylbutyric acid

B

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With potassium permanganate
dimethyl-oxalacetic acid
7346-12-5

dimethyl-oxalacetic acid

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With water; copper(II) ion Decarboxylation.pH 2-7;
With aluminium(III) ion; water Decarboxylation.pH 2-7;
With water; nickel(II) Decarboxylation.pH 2-7;
With water; manganese(II) Decarboxylation.pH 2-7;
at 25℃; Kinetics; Wss. Loesungen vom pH 0 bis pH 9, auch in Gegenwart verschiedener Metall-Ionen..Decarboxylation;
diethyl 3,3-dimethyl-2-ketosuccinate
5447-64-3

diethyl 3,3-dimethyl-2-ketosuccinate

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Conditions
ConditionsYield
With sulfuric acid
With hydrogenchloride
With hydrogen bromide; acetic acid
Sucrose
57-50-1

Sucrose

A

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

B

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With ammonium salts; Aspergillus niger; sulfite(2-)
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

Acetanilid
103-84-4

Acetanilid

N-(2-iso-butyrylphenyl)acetamide
1239986-59-4

N-(2-iso-butyrylphenyl)acetamide

Conditions
ConditionsYield
With ammonium peroxydisulfate; palladium(II) trifluoroacetate In diethylene glycol dimethyl ether at 20℃;93%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

(R)-3-((2S,3S)-3-Amino-2-hydroxy-4-phenyl-butyryl)-thiazolidine-4-carboxylic acid tert-butylamide; hydrochloride

(R)-3-((2S,3S)-3-Amino-2-hydroxy-4-phenyl-butyryl)-thiazolidine-4-carboxylic acid tert-butylamide; hydrochloride

(R)-3-[(2S,3S)-2-Hydroxy-3-(3-methyl-2-oxo-butyrylamino)-4-phenyl-butyryl]-thiazolidine-4-carboxylic acid tert-butylamide

(R)-3-[(2S,3S)-2-Hydroxy-3-(3-methyl-2-oxo-butyrylamino)-4-phenyl-butyryl]-thiazolidine-4-carboxylic acid tert-butylamide

Conditions
ConditionsYield
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine89%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

calcium 3-methyl-2-oxobutanoate

calcium 3-methyl-2-oxobutanoate

Conditions
ConditionsYield
Stage #1: 3-methyl-2-ketobutanoic acid With pyrographite; potassium hydroxide In water pH=7; Reflux; Large scale;
Stage #2: With calcium chloride In water at 0.2℃; for 3h; Solvent; Reagent/catalyst; Reflux; Large scale;
87.5%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

(S)-2-Hydroxy-3-methylbutanoic acid
17407-55-5

(S)-2-Hydroxy-3-methylbutanoic acid

Conditions
ConditionsYield
With NAD; hydrogen In hydrogenchloride for 42h; Ambient temperature;86%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

methyl 3-methyl-2-ketobutanoate
3952-67-8

methyl 3-methyl-2-ketobutanoate

Conditions
ConditionsYield
In diethyl ether at 0℃;84%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

4-methoxybenzoic acid hydrazide
3290-99-1

4-methoxybenzoic acid hydrazide

2-(4-Methoxybenzoylhydrazono)-3-methylbuttersaeure
152332-37-1

2-(4-Methoxybenzoylhydrazono)-3-methylbuttersaeure

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 60℃; for 2h;84%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

potassium phenyltrifluoborate

potassium phenyltrifluoborate

phenyl isopropyl ketone
611-70-1

phenyl isopropyl ketone

Conditions
ConditionsYield
With dipotassium peroxodisulfate; palladium diacetate In water; dimethyl sulfoxide at 20℃; for 3h;83%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

(S)-tert-butyl 2-(hydroxyamino)-3-methylbutanoate
1124196-10-6

(S)-tert-butyl 2-(hydroxyamino)-3-methylbutanoate

tert-butyl 2-(N-hydroxy-3-methyl-2-oxobutanamido)-3-methylbutanoate

tert-butyl 2-(N-hydroxy-3-methyl-2-oxobutanamido)-3-methylbutanoate

Conditions
ConditionsYield
Stage #1: 3-methyl-2-ketobutanoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 15h; Inert atmosphere;
Stage #2: (S)-tert-butyl 2-(hydroxyamino)-3-methylbutanoate With sodium carbonate In dichloromethane; water at 20℃; for 30h; Inert atmosphere;
82%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

3-Phenylpropenol
104-54-1

3-Phenylpropenol

cinnamyl 3-methyl-2-oxobutanoate

cinnamyl 3-methyl-2-oxobutanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane80%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

2-(aminocarbonyl)-1-pyrrolidinecarboxylic acid, phenylmethyl ester
93188-01-3

2-(aminocarbonyl)-1-pyrrolidinecarboxylic acid, phenylmethyl ester

Z-Pro-Δ Val
113586-10-0

Z-Pro-Δ Val

Conditions
ConditionsYield
toluene-4-sulfonic acid In benzene for 10h; Heating;75%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

(S)-2-amino-3-phenylpropionamide hydrochloride
65864-22-4

(S)-2-amino-3-phenylpropionamide hydrochloride

N-2-oxo-3-methylbutanoyl-L-phenylalanine amide

N-2-oxo-3-methylbutanoyl-L-phenylalanine amide

Conditions
ConditionsYield
Stage #1: (S)-2-amino-3-phenylpropionamide hydrochloride With triethylamine In dichloromethane at 4℃;
Stage #2: 3-methyl-2-ketobutanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 4 - 20℃; for 2.5h;
74%
allyltrichlorosilane
107-37-9

allyltrichlorosilane

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

2-hydroxy-2-isopropyl-pent-4-enoic acid

2-hydroxy-2-isopropyl-pent-4-enoic acid

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 15h; Addition;73%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

benzoic acid hydrazide
613-94-5

benzoic acid hydrazide

2-Benzoylhydrazono-3-methylbuttersaeure
173973-79-0

2-Benzoylhydrazono-3-methylbuttersaeure

Conditions
ConditionsYield
In water at 65℃; for 2h;70%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

methyl S-((3R,5R)-5-hydroxyoctan-3-yl)-L-cysteinate

methyl S-((3R,5R)-5-hydroxyoctan-3-yl)-L-cysteinate

methyl S-((3R,5R)-5-hydroxyoctan-3-yl)-N-(3-methyl-2-oxobutanoyl)-L-cysteinate

methyl S-((3R,5R)-5-hydroxyoctan-3-yl)-N-(3-methyl-2-oxobutanoyl)-L-cysteinate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In diethyl ether at 0 - 23℃; for 18h;70%
C6H4NCH2CHCCH2
491-35-0

C6H4NCH2CHCCH2

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

2-isopropyl-4-methylquinoline
91879-71-9

2-isopropyl-4-methylquinoline

Conditions
ConditionsYield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; tetraethylammonium hexafluorophosphate; trifluoroacetic acid In acetonitrile at 50℃; Schlenk technique; Electrochemical reaction; Irradiation; Inert atmosphere;68%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

O-benzyl carbamate
621-84-1

O-benzyl carbamate

2-(((benzyloxy)carbonyl)amino)-3-methylbut-2-enoic acid
95863-98-2

2-(((benzyloxy)carbonyl)amino)-3-methylbut-2-enoic acid

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene at 99.85℃; for 8h;67%
With toluene-4-sulfonic acid In benzene at 100℃; for 8h;67%
With toluene-4-sulfonic acid In benzene at 100℃; for 8h;67%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

phenylhydrazine
100-63-0

phenylhydrazine

phenyl isopropyl ketone
611-70-1

phenyl isopropyl ketone

Conditions
ConditionsYield
With oxygen; silver(I) acetate; lithium carbonate In 1,2-dichloro-ethane at 100℃; under 760.051 Torr; for 16h; Schlenk technique; Green chemistry;67%
1,4-pyrazine
290-37-9

1,4-pyrazine

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

2-methyl-1-(pyrazin-2-yl)propan-1-one
86461-66-7

2-methyl-1-(pyrazin-2-yl)propan-1-one

Conditions
ConditionsYield
With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; formic acid; dimethyl sulfoxide In dichloromethane; water at 40℃; Minisci Aromatic Substitution;65%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

2-Hydrazino-2-thiazolin-hydrobromid
2643-92-7

2-Hydrazino-2-thiazolin-hydrobromid

2,3-Dihydro-6-isopropyl-5H-thiazolo<2,3-c><1,2,4>-triazin-5-on
90516-89-5

2,3-Dihydro-6-isopropyl-5H-thiazolo<2,3-c><1,2,4>-triazin-5-on

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 18h; Heating;64%
4-Octyne
1942-45-6

4-Octyne

3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

(Z)-3-isopropyl-4-propyl-5-propylidenefuran-2(5H)-one

(Z)-3-isopropyl-4-propyl-5-propylidenefuran-2(5H)-one

Conditions
ConditionsYield
With tetrakis(acetonitrile)copper(I)tetrafluoroborate In toluene at 130℃; for 20h; Inert atmosphere; Sealed tube; diastereoselective reaction;64%
3-methyl-2-ketobutanoic acid
759-05-7

3-methyl-2-ketobutanoic acid

methyl S-((3R,5S)-5-hydroxyoctan-3-yl)-L-cysteinate

methyl S-((3R,5S)-5-hydroxyoctan-3-yl)-L-cysteinate

methyl S-((3R,5S)-5-hydroxyoctan-3-yl)-N-(3-methyl-2-oxobutanoyl)-L-cysteinate

methyl S-((3R,5S)-5-hydroxyoctan-3-yl)-N-(3-methyl-2-oxobutanoyl)-L-cysteinate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In diethyl ether at 0 - 23℃; for 18h;62%

759-05-7Relevant articles and documents

Photoinduced homolytic decarboxylative acylation/cyclization of unactivated alkenes with α-keto acid under external oxidant and photocatalyst free conditions: access to quinazolinone derivatives

Sun, Bin,Shi, Rongcheng,Zhang, Kesheng,Tang, Xiaoli,Shi, Xiayue,Xu, Jiayun,Yang, Jin,Jin, Can

supporting information, p. 6050 - 6053 (2021/06/21)

A novel and green strategy for the synthesis of acylated quinazolinone derivativesviaphoto-induced decarboxylative cascade radical acylation/cyclization of quinazolinone bearing unactivated alkenes has been developed. The protocol provides a novel route to access acyl radicals from α-keto acids through a self-catalyzed energy transfer process. Most importantly, the reaction proceeded smoothly without any external photocatalyst, additive or oxidant, and could be easily scaled-up in flow conditions with sunlight irradiation.

Exploration of Transaminase Diversity for the Oxidative Conversion of Natural Amino Acids into 2-Ketoacids and High-Value Chemicals

Chen, Yanchun,Cui, Xuexian,Cui, Yinglu,Li, Chuijian,Li, Ruifeng,Li, Tao,Sun, Jinyuan,Wu, Bian,Zhu, Tong

, p. 7950 - 7957 (2020/08/21)

The use of 2-ketoacids is very common in feeds, food additives, and pharmaceuticals, and 2-ketoacids are valuable precursors for a plethora of chemically diverse compounds. Biocatalytic synthesis of 2-ketoacids starting from l-amino acids would be highly desirable because the substrates are readily available from biomass feedstock. Here, we report bioinformatic exploration of a series of aminotransferases (ATs) to achieve the desired conversion. Thermodynamic control was achieved by coupling an l-glutamate oxidation reaction in the cascade for the recycling of the amine acceptor. These enzymes were able to convert a majority of proteinogenic amino acids into the corresponding 2-ketoacids with high conversion (up to 99percent) and atom-efficiency. Furthermore, this enzyme cascade was extendable, and one-pot two-step processes were established for the synthesis of d-amino acids and N-methylated amino acids, achieving great overall conversion (up to 99percent) and high ee values (>99percent). These developed enzymatic methodologies offer convenient routes for utilizing amino acids as synthetic reagents.

Synthesis method of 2-(9H-fluorene-9-methoxycarbonylamino)-3-methyl-2-butenoic acid

-

Paragraph 0006; 0009, (2020/12/30)

The invention relates to a synthesis method of 2-(9H-fluorene-9-methoxycarbonylamino)-3-methyl-2-butenoic acid. The method mainly solves the technical problem of lack of an amplified production methodof 2-(9H-fluorene-9-methoxycarbonylamino)-3-methyl-2-butenoic acid at present. The synthesis method comprises the following steps: in methyl tert-butyl ether cooled in an ice bath, acidifying 3-methyl-2-oxobutyrate with concentrated hydrochloric acid to generate a compound 1; in methylbenzene subjected to heating reflux, the compound 1 and fluorenylmethoxycarbonylamide are subjected to dehydration condensation reaction under the catalytic action of p-toluenesulfonic acid to generate a target compound 2. As a medical intermediate and a dehydroamino acid derivative, 2-(9H-fluorene-9-methoxycarbonylamino)-3-methyl-2-butenoic acid is widely applied to the fields of synthesis of peptide active substances and protein engineering.

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