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124044-13-9

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124044-13-9 Usage

General Description

Carbopenem intermediate is a chemical intermediate in the production of carbopenem antibiotics, a class of broad-spectrum antibiotics used to treat a variety of bacterial infections. This intermediate is crucial in the synthesis of carbopenem antibiotics and is used in the pharmaceutical industry for the manufacturing of these drugs. It is a key building block in the production of important antibiotics that are used to combat a wide range of bacterial pathogens, and its production and use are tightly regulated to ensure the quality and safety of the resulting pharmaceutical products.

Check Digit Verification of cas no

The CAS Registry Mumber 124044-13-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,4,0,4 and 4 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 124044-13:
(8*1)+(7*2)+(6*4)+(5*0)+(4*4)+(3*4)+(2*1)+(1*3)=79
79 % 10 = 9
So 124044-13-9 is a valid CAS Registry Number.

124044-13-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate

1.2 Other means of identification

Product number -
Other names methyl (2S,3R)-2-benzamidomethyl-3-hydroxybutanoate

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:124044-13-9 SDS

124044-13-9Synthetic route

methyl 2-[(N-benzoylamino)methyl]-3-oxobutyrate
129994-60-1

methyl 2-[(N-benzoylamino)methyl]-3-oxobutyrate

methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate
124044-13-9

methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate

Conditions
ConditionsYield
In hexane; dichloromethane; nitrogen; ethyl acetate90%
In hexane; dichloromethane; ethyl acetate87%
With hydrogen; (R)-3,5-t-Bu2-binap-RuI2 In methanol; dichloromethane at 50 - 60℃; under 38000 Torr; for 40h; Product distribution; other cationic binap-ruthenium(II) catalysts, var. solvents, reaction time, substrate/catalyst ratio; diastereoselectivity and enantioselectivity of the reduction;55%
methyl 2-[(N-benzoylamino)methyl]-3-oxobutyrate
129994-60-1

methyl 2-[(N-benzoylamino)methyl]-3-oxobutyrate

A

methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate
124044-13-9

methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate

B

(2R,3S)-methyl 2-(benzamidomethyl)-3-hydroxybutanoate
129994-65-6

(2R,3S)-methyl 2-(benzamidomethyl)-3-hydroxybutanoate

C

anti-(2R,3R)-Methyl 2-(benzamidomethyl)-3-hydroxybutanoate
135138-76-0

anti-(2R,3R)-Methyl 2-(benzamidomethyl)-3-hydroxybutanoate

D

(2S,3S)-methyl-2-benzamido-methyl-3-hydroxybutyrate
145588-28-9

(2S,3S)-methyl-2-benzamido-methyl-3-hydroxybutyrate

Conditions
ConditionsYield
With hydrogen; (p-cymene)>I In methanol at 65℃; under 41040 Torr; for 20h; Product distribution; Ru(II)-asymmetric hydrogenation, diastereoselectivity and enantioselectivity, effect of solvents;
With hydrogen; <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3 at 50℃; under 76000.1 Torr; for 20h; Yields of byproduct given. Title compound not separated from byproducts;
methyl 2-[(N-benzoylamino)methyl]-3-oxobutyrate
129994-60-1

methyl 2-[(N-benzoylamino)methyl]-3-oxobutyrate

A

methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate
124044-13-9

methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate

B

anti-(2R,3R)-Methyl 2-(benzamidomethyl)-3-hydroxybutanoate
135138-76-0

anti-(2R,3R)-Methyl 2-(benzamidomethyl)-3-hydroxybutanoate

Conditions
ConditionsYield
With hydrogen; I In methanol at 50℃; under 38000 Torr; for 20h; Product distribution; other: catalysts, solvents, time, pressure;
With hydrogen; I In methanol; dichloromethane at 65℃; under 41040 Torr; for 21h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogen; I In methanol; dichloromethane at 50 - 60℃; under 38000 Torr; for 40h; Yield given. Yields of byproduct given;
With hydrogen; I In methanol at 50℃; under 38000 Torr; for 20h; Yield given. Yields of byproduct given;
methyl 2-[(N-benzoylamino)methyl]-3-oxobutyrate
129994-60-1

methyl 2-[(N-benzoylamino)methyl]-3-oxobutyrate

A

methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate
124044-13-9

methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate

B

(2R,3S)-methyl 2-(benzamidomethyl)-3-hydroxybutanoate
129994-65-6

(2R,3S)-methyl 2-(benzamidomethyl)-3-hydroxybutanoate

C

anti-(2R,3R)-Methyl 2-(benzamidomethyl)-3-hydroxybutanoate
135138-76-0

anti-(2R,3R)-Methyl 2-(benzamidomethyl)-3-hydroxybutanoate

Conditions
ConditionsYield
With hydrogen; <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3 at 50℃; under 76000.1 Torr; for 20h; Yields of byproduct given. Title compound not separated from byproducts;
(2S)-methyl-2-benzamido-methyl-3-oxobutanoate

(2S)-methyl-2-benzamido-methyl-3-oxobutanoate

methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate
124044-13-9

methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate

Conditions
ConditionsYield
With glucose dehydrogenase; alpha-D-glucopyranose; BgADH2 enzyme; nicotinamide adenine dinucleotide phosphate In water; toluene at 35℃; for 8h; pH=6.5; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;n/a
methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate
124044-13-9

methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate

(2S,3R)-2-aminomethyl-3-hydroxybutanoic acid hydrochloride
129994-66-7

(2S,3R)-2-aminomethyl-3-hydroxybutanoic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride93%
methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate
124044-13-9

methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With hydrogenchloride93%
methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate
124044-13-9

methyl (2S,3R)-2-[(N-benzoylamino)-methyl]-3-hydroxybutyrate

(2S)-3-amino-2-((1R)-1-hydroxyethyl)propionic acid
120236-27-3

(2S)-3-amino-2-((1R)-1-hydroxyethyl)propionic acid

Conditions
ConditionsYield
With triethylamine In 12N-hydrochloric acid; toluene; acetonitrile80%

124044-13-9Relevant articles and documents

Preparation method of 4AA

-

Paragraph 0016; 0018; 0021; 0024, (2021/07/28)

The invention discloses a preparation method of 4AA. The preparation method comprises the following steps: S1, preparing a first intermediate from benzamide and a formaldehyde aqueous solution; S2, preparing a second intermediate from the first intermediate, thionyl chloride, toluene and n-heptane; S3, preparing a third intermediate from the second intermediate, methyl acetoacetate, sodium methoxide, toluene, diluted hydrochloric acid and isopropanol; S4, preparing a fourth intermediate from the third intermediate, reductase, ethyl acetate, saturated sodium bicarbonate and saturated salt water; S5, preparing a fifth intermediate from the fourth intermediate, imidazole, TBSCL and methylbenzene; S6, preparing a sixth intermediate from the fifth intermediate, ethanolamine, methanol and n-heptane; S7, preparing a seventh intermediate by using the sixth intermediate, a Grignard reagent and n-heptane; and S8, preparing 4AA from the seventh intermediate, ruthenium trichloride, potassium acetate, ethyl acetate, acetic acid and a peracetic acid solution.

Asymmetric synthesis of optically active methyl-2-benzamido-methyl-3-hydroxy-butyrate by robust short-chain alcohol dehydrogenases from Burkholderia gladioli

Chen, Xiang,Liu, Zhi-Qiang,Huang, Jian-Feng,Lin, Chao-Ping,Zheng, Yu-Guo

supporting information, p. 12328 - 12331 (2015/07/27)

Three short-chain alcohol dehydrogenases from Burkholderia gladioli were discovered for their great potential in the dynamic kinetic asymmetric transformation of methyl 2-benzamido-methyl-3-oxobutanoate, and their screening against varied organic solvents and substrates. This is the first report of recombinant enzymes capable of achieving this reaction with the highest enantio- and diastereo-selectivity.

New Chiral Diphosphine Ligands Designed to Have a Narrow Dihedral Angle in the Biaryl Backbone

Saito, Takao,Yokozawa, Tohru,Ishizaki, Takero,Moroi, Takashi,Sayo, Noboru,Miura, Takashi,Kumobayashi, Hidenori

, p. 264 - 267 (2007/10/03)

A series of novel optically active diphosphine ligands, (4,4′-bi-1,3-benzodioxole)-5,5′-diylbis(diarylphosphine)s (6), which are called SEGPHOS, has been designed and synthesized with dihedral angles in the Ru complexes being less than that in the corresponding BINAP-Ru complex. The stereorecognition abilities of SEGPHOS-Ru complex catalysts in the asymmetric catalytic hydrogenation of a wide variety of carbonyl compounds are superior to those observed with BINAP-Ru complex catalysts.

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