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Cas Database

42429-20-9

42429-20-9

Identification

  • Product Name:Benzeneacetic acid, a-(acetylamino)-, (aS)-

  • CAS Number: 42429-20-9

  • EINECS:

  • Molecular Weight:193.202

  • Molecular Formula: C10H11NO3

  • HS Code:

  • Mol File:42429-20-9.mol

Synonyms:N-Acetyl-L-phenylglycine;(2S)-2-(Acetylamino)-2-phenylacetic acid;(2S)-2-Acetylamino-2-phenylacetic acid;(S)-(Acetylamino)phenylacetic acid;(αS)-α-(Acetylamino)benzeneacetic acid;Benzeneacetic acid, a-(acetylaMino)-, (S)-;(S)-N-Acetyl-2-phenylglycine;N-Acetyl-(S)-2-phenylglycine

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:Crysdot
  • Product Description:(S)-2-Acetamido-2-phenylaceticacid 95+%
  • Packaging:1g
  • Price:$ 189
  • Delivery:In stock
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  • Manufacture/Brand:Chemenu
  • Product Description:(S)-2-acetamido-2-phenylaceticacid 95%
  • Packaging:1g
  • Price:$ 184
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:(S)-2-Acetamido-2-phenylacetic acid
  • Packaging:2 g
  • Price:$ 340
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:(S)-2-Acetamido-2-phenylacetic acid
  • Packaging:1 g
  • Price:$ 200
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:(S)-2-Acetamido-2-phenylacetic acid
  • Packaging:5 g
  • Price:$ 680
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:(S)-2-Acetamido-2-phenylacetic acid
  • Packaging:500 mg
  • Price:$ 115
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:(S)-2-Acetamido-2-phenylacetic acid
  • Packaging:250 mg
  • Price:$ 65
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  • Manufacture/Brand:Ambeed
  • Product Description:(S)-2-Acetamido-2-phenylaceticacid 95%
  • Packaging:1g
  • Price:$ 31
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  • Manufacture/Brand:Ambeed
  • Product Description:(S)-2-Acetamido-2-phenylaceticacid 95%
  • Packaging:250mg
  • Price:$ 13
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  • Manufacture/Brand:Ambeed
  • Product Description:(S)-2-Acetamido-2-phenylaceticacid 95%
  • Packaging:100mg
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Relevant articles and documentsAll total 45 Articles be found

GRANZYME B DIRECTED IMAGING AND THERAPY

-

Page/Page column 82; 105, (2019/09/04)

Provided herein are heterocyclic compounds useful for imaging Granzyme B. Methods of imaging Granzyme B, combination therapies, and kits comprising the Granzyme B imaging agents are also provided.

Chemo- and Enantioselective Pd/B Hybrid Catalysis for the Construction of Acyclic Quaternary Carbons: Migratory Allylation of O-Allyl Esters to α- C-Allyl Carboxylic Acids

Fujita, Taiki,Yamamoto, Tomohiro,Morita, Yuya,Chen, Hongyu,Shimizu, Yohei,Kanai, Motomu

supporting information, p. 5899 - 5903 (2018/05/14)

We describe herein the asymmetric synthesis of α-allyl carboxylic acids containing an α-quaternary stereocenter by a chiral hybrid catalyst system comprising palladium and boron complexes. The reaction proceeded through palladium-catalyzed ionization of α,α-disubstituted O-allyl esters for the generation of chiral π-allyl palladium complex as an electrophile, boron-catalyzed enolization of the carboxylate part for the generation of chiral α,α-disubstituted carboxylic acid-derived enolates as a nucleophile, and enantioselective coupling between the thus-generated nucleophile and electrophile. Proper combinations of chiral ligands for the boron and palladium catalysts were crucial. The reaction proceeded chemoselectively at the α-position of the carboxylic acid group.

Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

Wang, Tianli,Yu, Zhaoyuan,Hoon, Ding Long,Phee, Claire Yan,Lan, Yu,Lu, Yixin

supporting information, p. 265 - 271 (2016/01/25)

Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective γ-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective γ-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronucleophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective γ-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched α,α-disubstituted α-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and γ-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic oxazolide and the electrophilic phosphonium intermediate.

Chemical resolution of DL-phenylalanine methyl ester using N-acetyl-D-phenylglycine as resolving agent

Wang, Shuai-Shuai,Zou, Fang,Meng, Wen-Qi,Zhang, Jing-Zheng,Feng, Yan,Zhang, Ling,Liu, Yi

, p. 159 - 161 (2015/06/02)

An improved method for chemical resolution of DL-phenylalanine methyl ester using N-acetyl-D-phenylglycine as a resolving agent is described. This new resolving agent is readily available, non-toxic and easily recoverable from the insoluble diasteromeric salt. This method was used to obtain D-phenylalanine methyl ester with high optical purity of 98.1% and a high yield of 81.2%.

Synthesis, enantioresolution, and activity profile of chiral 6-methyl-2,4-disubstituted pyridazin-3(2H)-ones as potent N-formyl peptide receptor agonists

Cilibrizzi, Agostino,Schepetkin, Igor A.,Bartolucci, Gianluca,Crocetti, Letizia,Dal Piaz, Vittorio,Giovannoni, Maria Paola,Graziano, Alessia,Kirpotina, Liliya N.,Quinn, Mark T.,Vergelli, Claudia

experimental part, p. 3781 - 3792 (2012/08/28)

A series of chiral pyridazin-3(2H)-ones was synthesized, separated as pure enantiomers, and evaluated for N-formyl peptide receptor (FPR) agonist activity. Characterization of the purified enantiomers using combined chiral HPLC and chiroptical studies (circular dichroism, allowed unambiguous assignment of the absolute configuration for each pair of enantiomers). Evaluation of the ability of racemic mixtures and purified enantiomers to stimulate intracellular Ca 2+ flux in FPR-transfected HL-60 cells and human neutrophils and to induce β-arrestin recruitment in FPR-transfected CHO-K1 cells showed that many enantiomers were potent agonists, inducing responses in the sub-micromolar to nanomolar range. Furthermore, FPRs exhibited enantiomer selectivity, generally preferring the R-(-)-forms over the S-(+)-enantiomers. Finally, we found that elongation of the carbon chain in the chiral center of the active compounds generally increased biological activity. Thus, these studies provide important new information regarding molecular features involved in FPR ligand preference and report the identification of a novel series of FPR agonists.

Process route upstream and downstream products

Process route

phenylglycin
2835-06-5

phenylglycin

(R)-(-)-N-acetylphenylglycine
14257-84-2,15962-46-6,29633-99-6,42429-20-9

(R)-(-)-N-acetylphenylglycine

Benzoylformic acid
611-73-4

Benzoylformic acid

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
bei der Einw. von gaerender Hefe;
(S)-2-phenylglycine
2935-35-5

(S)-2-phenylglycine

(R)-(-)-N-acetylphenylglycine
14257-84-2,15962-46-6,29633-99-6,42429-20-9

(R)-(-)-N-acetylphenylglycine

Conditions
Conditions Yield
With lipase A from Candida antarctica (Chirazyme L5) from Roche; at 20 ℃; for 24h; pH=7.5; enantioselective reaction; aq. phosphate buffer; Enzymatic reaction;
With cobalt(II) chloride; at 30 ℃; pH=8; optical yield given as %ee; enantioselective reaction; aq. phosphate buffer; Resolution of racemate; Enzymatic reaction;
With lipase AS 'Amano'; at 35 ℃; for 24h; pH=6.5; enantioselective reaction; Enzymatic reaction;
96 % ee
phenylglycin
2835-06-5

phenylglycin

(S)-2-phenylglycine
2935-35-5

(S)-2-phenylglycine

(R)-(-)-N-acetylphenylglycine
14257-84-2,15962-46-6,29633-99-6,42429-20-9

(R)-(-)-N-acetylphenylglycine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: triethylamine / water; N,N-dimethyl-formamide / 20 °C
2: lipase AS 'Amano' / 24 h / 35 °C / pH 6.5 / Enzymatic reaction
With lipase AS 'Amano'; triethylamine; In water; N,N-dimethyl-formamide;
2-Methyl-5-oxo-4-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester
162247-66-7

2-Methyl-5-oxo-4-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

(S)-2-phenylglycine
2935-35-5

(S)-2-phenylglycine

(R)-(-)-N-acetylphenylglycine
14257-84-2,15962-46-6,29633-99-6,42429-20-9

(R)-(-)-N-acetylphenylglycine

(S)-N-acetyl-2-phenylglycine
14257-84-2,15962-46-6,29633-99-6,42429-20-9

(S)-N-acetyl-2-phenylglycine

Conditions
Conditions Yield
With sodium hydroxide; In ethanol; for 0.5h; Yield given. Yields of byproduct given; Heating;
2-Methyl-5-oxo-4-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester
162247-66-7

2-Methyl-5-oxo-4-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

(S)-2-phenylglycine
2935-35-5

(S)-2-phenylglycine

(R)-(-)-N-acetylphenylglycine
14257-84-2,15962-46-6,29633-99-6,42429-20-9

(R)-(-)-N-acetylphenylglycine

(S)-N-acetyl-2-phenylglycine
14257-84-2,15962-46-6,29633-99-6,42429-20-9

(S)-N-acetyl-2-phenylglycine

Conditions
Conditions Yield
With sodium hydroxide; In ethanol; for 0.5h; Yield given. Yields of byproduct given; Heating;
acetamide
60-35-5

acetamide

carbon monoxide
201230-82-2

carbon monoxide

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
With lithium bromide monohydrate; sulfuric acid; palladium(II) bromide; at 80 ℃; for 12h; Ionic liquid;
98%
With 1-methyl-pyrrolidin-2-one; sulfuric acid; lithium bromide; bis(triphenylphosphine)palladium dibromide; at 120 ℃; for 15h; under 45003.6 Torr;
92%
With sulfuric acid; lithium bromide; bis(triphenylphosphine)palladium dibromide; In various solvent(s); at 120 ℃; for 12h; under 45003.6 Torr;
85%
With polymer incarcerated Pd(PPh3)4; sulfuric acid; benzyltriethylammonium bromide; In 1,4-dioxane; at 120 ℃; for 6h; under 45600 Torr;
78%
With 1-methyl-pyrrolidin-2-one; sulfuric acid; lithium bromide; palladium on activated charcoal; at 120 ℃; for 12h; under 45003.6 Torr;
74%
With 1-methyl-pyrrolidin-2-one; sulfuric acid; lithium bromide; bis(triphenylphosphine)palladium dibromide; hydroquinone; In water; at 120 ℃; for 14h; under 45003.6 Torr;
65%
With 3-ethyl-1-methyl-1H-imidazol-3-ium bromide; triphenylphosphine; palladium(II) bromide; at 100 ℃; for 15h; under 45004.5 Torr;
53%
With sulfuric acid; triphenylphosphine; lithium bromide; HZSM-5 zeolite; palladium; In 1-methyl-pyrrolidin-2-one; toluene; at 90 ℃; for 16h; under 45003.6 Torr;
40%
With hydrogenchloride; potassium tetrachloroplatinate; triphenylphosphine; In 1,4-dioxane; at 120 ℃; for 15h; under 45600 Torr;
32%
acetic anhydride
108-24-7

acetic anhydride

phenylglycin
2835-06-5

phenylglycin

Conditions
Conditions Yield
With sodium hydroxide;
92%
With sodium hydrogencarbonate; In 1,4-dioxane; water; Yield given; Ambient temperature;
In alkaline aq. solution; at 4 ℃; for 0.5h; pH=11;
In methanol; at 20 ℃;
3.6 g
With triethylamine; In water; N,N-dimethyl-formamide; at 20 ℃;
NaOH-dissolved

NaOH-dissolved

phenylglycin
2835-06-5

phenylglycin

Conditions
Conditions Yield
With sodium hydroxide; acetic anhydride; In water-are; water;
553 g (87%)
Conditions
Conditions Yield
With tricyclohexylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer; In acetonitrile; at 60 ℃; for 48h;
acetyl chloride
75-36-5

acetyl chloride

phenylglycin
2835-06-5

phenylglycin

Conditions
Conditions Yield
With sodium carbonate; In 1,4-dioxane; water; at 20 ℃; Inert atmosphere;

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