Welcome to LookChem.com Sign In|Join Free

Cas Database

72776-05-7

72776-05-7

Identification

  • Product Name:2-Azetidinecarboxylicacid, 4-oxo-, phenylmethyl ester, (2S)-

  • CAS Number: 72776-05-7

  • EINECS:

  • Molecular Weight:205.213

  • Molecular Formula: C11H11 N O3

  • HS Code:29337900

  • Mol File:72776-05-7.mol

Synonyms:2-Azetidinecarboxylicacid, 4-oxo-, phenylmethyl ester, (S)-; Benzyl (S)-4-oxo-2-azetidinecarboxylate

Post Buying Request Now
Entrust LookChem procurement to find high-quality suppliers faster

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

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:TRC
  • Product Description:Benzyl(2S)-4-Oxoazetidine-2-carboxylate
  • Packaging:1g
  • Price:$ 160
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TRC
  • Product Description:Benzyl(2S)-4-Oxoazetidine-2-carboxylate
  • Packaging:500mg
  • Price:$ 80
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Benzyl (S)-(?)-4-oxo-2-azetidinecarboxylate 97%
  • Packaging:5g
  • Price:$ 253
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Crysdot
  • Product Description:(S)-Benzyl4-oxoazetidine-2-carboxylate 95+%
  • Packaging:5g
  • Price:$ 270
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Chemenu
  • Product Description:(S)-Benzyl2-azetidinone-4-carboxylate 95%
  • Packaging:5g
  • Price:$ 252
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Benzyl (S)-4-oxo-2-azetidinecarboxylate
  • Packaging:5 g
  • Price:$ 250
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Benzyl (S)-4-oxo-2-azetidinecarboxylate
  • Packaging:1 g
  • Price:$ 70
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Benzyl (S)-4-oxo-2-azetidinecarboxylate
  • Packaging:2 g
  • Price:$ 120
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Benzyl (S)-4-oxo-2-azetidinecarboxylate
  • Packaging:10 g
  • Price:$ 450
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Benzyl (S)-4-oxo-2-azetidinecarboxylate
  • Packaging:25 g
  • Price:$ 1000
  • Delivery:In stock
  • Buy Now

Relevant articles and documentsAll total 17 Articles be found

RETRACTED ARTICLE: Site-selective enzymatic C-H amidation for synthesis of diverse lactams

Cho, Inha,Jia, Zhi-Jun,Arnold, Frances H.

, p. 575 - 578 (2019/06/07)

A major challenge in carbon?hydrogen (C?H) bond functionalization is to have the catalyst control precisely where a reaction takes place. In this study, we report engineered cytochrome P450 enzymes that perform unprecedented enantioselective C?H amidation reactions and control the site selectivity to divergently construct b-, g-, and d-lactams, completely overruling the inherent reactivities of the C?H bonds. The enzymes, expressed in Escherichia coli cells, accomplish this abiological carbon?nitrogen bond formation via reactive iron-bound carbonyl nitrenes generated from nature-inspired acyl-protected hydroxamate precursors. This transformation is exceptionally efficient (up to 1,020,000 total turnovers) and selective (up to 25:1 regioselectivity and 97%, please refer to compound 2v enantiomeric excess), and can be performed easily on preparative scale.

The discovery and optimization of benzimidazoles as selective NaV1.8 blockers for the treatment of pain

Brown, Alan D.,Bagal, Sharan K.,Blackwell, Paul,Blakemore, David C.,Brown, Bruce,Bungay, Peter J.,Corless, Martin,Crawforth, James,Fengas, David,Fenwick, David R.,Gray, Victoria,Kemp, Mark,Klute, Wolfgang,Malet Sanz, Laia,Miller, Duncan,Murata, Yoshihisa,Payne, C. Elizabeth,Skerratt, Sarah,Stevens, Edward B.,Warmus, Joseph S.

, p. 230 - 239 (2018/12/11)

The voltage gated sodium channel NaV1.8 has been postulated to play a key role in the transmission of pain signals. Core hopping from our previously reported phenylimidazole leads has allowed the identification of a novel series of benzimidazole NaV1.8 blockers. Subsequent optimization allowed the identification of compound 9, PF-06305591, as a potent, highly selective blocker with an excellent preclinical in vitro ADME and safety profile.

Targeting integrins αvβ3 and α5β1 with new β-lactam derivatives

Galletti, Paola,Soldati, Roberto,Pori, Matteo,Durso, Margherita,Tolomelli, Alessandra,Gentilucci, Luca,Dattoli, Samantha Deianira,Baiula, Monica,Spampinato, Santi,Giacomini, Daria

, p. 284 - 293 (2014/07/08)

The αvβ3 and α5β 1 integrins are widely expressed in different cancer types and recognize the tripeptide Arg-Gly-Asp (RGD) motif present in several extracellular matrix proteins. We report here the design, synthesis and biological activity of some new β-lactam derivatives specifically designed to target integrins. The new molecules contain the azetidinone as the only cyclic framework armed with carboxylic acid and amine terminals spaced from 9 to 14 atoms to switch on recognition by integrins. All tested molecules showed a concentration-dependent enhancement in fibronectin-mediated adhesion of K562 and SK-MEL-24 cells; in particular 1, expressed a higher affinity towards α5β1 integrin (EC50 of 12 nM) and 2 was more selective for integrin αvβ3 (EC 50 of 11 nM).

Cyclic dipeptides and azetidinone compounds and their use in treating CNS injury and neurodegenerative disorders

-

Page/Page column 45, (2010/11/26)

The present invention provides 4-substituted-2-azetidinone compounds, bicyclic 2-5-diketopiperazine compounds, and pharmaceutical compositions thereof that are potent, safe and effective neuroprotective agents. Due to their strong central nervous system (CNS) activity, the compounds can be used to enhance memory and to treat a variety of neurological disorders. The compounds are particularly useful for treating neurological disorders caused by, or associated with, CNS trauma.

β-Lactam derivatives as enzyme inhibitors: N-substituted derivatives of (S)-4-oxoazetidine-2-carboxylate as inhibitors of elastase and papain

Achilles,Schneider,Schirmeister,Otto

, p. 798 - 802 (2007/10/03)

N-Alkyl and N-acyl substituted 4-oxoazetidine-2-carboxylates are synthesized and evaluated as inhibitors of the proteases porcine pancreatic elastase (PPE) and papain. The compounds are obtained by alkylation or acylation at the nitrogen of benzyl (S)-4-oxoazetidine-2-carboxylate, which is synthesized by a modified literature procedure. The enzymatic assays prove some derivatives to be effective inhibitors of PPE and/or papain. The N-BOC protected amino acid derivatives 10 and 13 inhibit PPE reversibly with K(I)-values in the micromolar range. On the other hand, papain is inactivated irreversibly by benzyl (S)-2-(benzyloxycarbonyl)azetidin-1-acetate (6).

Process route upstream and downstream products

Process route

dibenzyl L-aspartate
2791-79-9

dibenzyl L-aspartate

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions
Conditions Yield
dibenzyl L-aspartate; With chloro-trimethyl-silane; triethylamine; In diethyl ether; at 0 ℃; for 1h;
With tert-butylmagnesium chloride; In diethyl ether; at -5 - 0 ℃; for 2h;
47%
dibenzyl L-aspartate; With chloro-trimethyl-silane; In diethyl ether; at -78 - 25 ℃;
With tert-butylmagnesium bromide; In diethyl ether; at -78 - 25 ℃;
40%
With chloro-trimethyl-silane; tert-butylmagnesium chloride;
With hydrogenchloride; chloro-trimethyl-silane; tert-butylmagnesium chloride; ammonium chloride; triethylamine; Yield given. Multistep reaction; 1.) Et2O, 0 deg C, 1 h, 2.) 0 deg C, overnight;
Multi-step reaction with 2 steps
1: triethylamine / diethyl ether / Ambient temperature
2: t-butylmagnesium chloride / diethyl ether / 0 °C
With tert-butylmagnesium chloride; triethylamine; In diethyl ether;
Multi-step reaction with 2 steps
1: Et3N / diethyl ether / 0 °C
2: tert-butylmagnesium chloride / 1.) 0 deg C, 2.) room temperature, overnight
With tert-butylmagnesium chloride; triethylamine; In diethyl ether;
Multi-step reaction with 2 steps
1: triethylamine / diethyl ether / 1 h / 0 °C
2: t-butylmagnesium chloride / diethyl ether / 0 °C
With tert-butylmagnesium chloride; triethylamine; In diethyl ether;
dibenzyl L-aspartate; With chloro-trimethyl-silane; triethylamine;
With tert-butylmagnesium chloride; In diethyl ether;
(L)-N-(trimethylsilyl)dibenzyl aspartate
72776-06-8

(L)-N-(trimethylsilyl)dibenzyl aspartate

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions
Conditions Yield
With tert-butylmagnesium chloride; In diethyl ether; at 0 ℃; Yield given;
With tert-butylmagnesium chloride; Yield given; 1.) 0 deg C, 2.) room temperature, overnight;
With tert-butylmagnesium chloride; In diethyl ether; at 0 ℃;
With tert-butylmagnesium chloride; In diethyl ether; at -5 - 20 ℃; for 12.5h;
5.1 g
C<sub>16</sub>H<sub>21</sub>NO<sub>5</sub>

C16H21NO5

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions
Conditions Yield
With cytochrome P411 expressed in Escherichia coli; In aq. phosphate buffer; at 20 ℃; for 24h; pH=8; enantioselective reaction; Catalytic behavior; Enzymatic reaction;
96 % ee
dibenzyl L-aspartate
2791-79-9

dibenzyl L-aspartate

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: TEA; 4-dimethylaminopyridine / diethyl ether / 3 h / 0 °C
2: 5.1 g / tBuMgCl / diethyl ether / 12.5 h / -5 - 20 °C
With dmap; TEA; tert-butylmagnesium chloride; In diethyl ether;
D-aspartic acid dibenzyl ester
4079-59-8

D-aspartic acid dibenzyl ester

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions
Conditions Yield
With chloro-trimethyl-silane; tert-butylmagnesium bromide; triethylamine; Yield given. Multistep reaction;
(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions
Conditions Yield
dibenzyl L-aspartate
2791-79-9

dibenzyl L-aspartate

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions
Conditions Yield
dibenzyl L-aspartate
2791-79-9

dibenzyl L-aspartate

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions
Conditions Yield
dibenzyl L-aspartate; With chloro-trimethyl-silane; triethylamine; In diethyl ether; at 0 ℃; for 1h;
With tert-butylmagnesium chloride; In diethyl ether; at -5 - 0 ℃; for 2h;
47%
dibenzyl L-aspartate; With chloro-trimethyl-silane; In diethyl ether; at -78 - 25 ℃;
With tert-butylmagnesium bromide; In diethyl ether; at -78 - 25 ℃;
40%
With chloro-trimethyl-silane; tert-butylmagnesium chloride;
With hydrogenchloride; chloro-trimethyl-silane; tert-butylmagnesium chloride; ammonium chloride; triethylamine; Yield given. Multistep reaction; 1.) Et2O, 0 deg C, 1 h, 2.) 0 deg C, overnight;
Multi-step reaction with 2 steps
1: triethylamine / diethyl ether / Ambient temperature
2: t-butylmagnesium chloride / diethyl ether / 0 °C
With tert-butylmagnesium chloride; triethylamine; In diethyl ether;
Multi-step reaction with 2 steps
1: Et3N / diethyl ether / 0 °C
2: tert-butylmagnesium chloride / 1.) 0 deg C, 2.) room temperature, overnight
With tert-butylmagnesium chloride; triethylamine; In diethyl ether;
Multi-step reaction with 2 steps
1: triethylamine / diethyl ether / 1 h / 0 °C
2: t-butylmagnesium chloride / diethyl ether / 0 °C
With tert-butylmagnesium chloride; triethylamine; In diethyl ether;
dibenzyl L-aspartate; With chloro-trimethyl-silane; triethylamine;
With tert-butylmagnesium chloride; In diethyl ether;
(L)-N-(trimethylsilyl)dibenzyl aspartate
72776-06-8

(L)-N-(trimethylsilyl)dibenzyl aspartate

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions
Conditions Yield
With tert-butylmagnesium chloride; In diethyl ether; at 0 ℃; Yield given;
With tert-butylmagnesium chloride; Yield given; 1.) 0 deg C, 2.) room temperature, overnight;
With tert-butylmagnesium chloride; In diethyl ether; at 0 ℃;
With tert-butylmagnesium chloride; In diethyl ether; at -5 - 20 ℃; for 12.5h;
5.1 g
C<sub>16</sub>H<sub>21</sub>NO<sub>5</sub>

C16H21NO5

(S)-benzyl 4-oxoazetidine-2-carboxylate
72776-05-7

(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions
Conditions Yield
With cytochrome P411 expressed in Escherichia coli; In aq. phosphate buffer; at 20 ℃; for 24h; pH=8; enantioselective reaction; Catalytic behavior; Enzymatic reaction;
96 % ee

Global suppliers and manufacturers

Global( 58) Suppliers
  • Company Name
  • Business Type
  • Contact Tel
  • Emails
  • Main Products
  • Country
  • Simagchem Corporation
  • Business Type:Manufacturers
  • Contact Tel:+86-592-2680277
  • Emails:sale@simagchem.com
  • Main Products:110
  • Country:China (Mainland)
  • Amadis Chemical Co., Ltd.
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-89925085
  • Emails:sales@amadischem.com
  • Main Products:29
  • Country:China (Mainland)
  • Shaanxi BLOOM TECH Co.,Ltd
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-29-86470566
  • Emails:sales@bloomtechz.com
  • Main Products:80
  • Country:China (Mainland)
  • LIDE PHARMACEUTICALS LIMITED
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-25-58409506
  • Emails:lide@lidepharma.com
  • Main Products:56
  • Country:China (Mainland)
  • SAGECHEM LIMITED
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-571-86818502
  • Emails:will@sagechem.com
  • Main Products:28
  • Country:China (Mainland)
  • Kono Chem Co.,Ltd
  • Business Type:Other
  • Contact Tel:86-29-86107037-8015
  • Emails:info@konochemical.com
  • Main Products:83
  • Country:China (Mainland)
  • Aecochem Corp.
  • Business Type:Manufacturers
  • Contact Tel:+86-592 599 8717
  • Emails:sales@aecochemical.com
  • Main Products:70
  • Country:China (Mainland)
close

Please post your buying leads,so that our qualified suppliers will soon contact you!

*Required Fields

CAS No.:
* Product Name:
* Your email:

Your email will be used to sign-in to LookChem.com
* Requirements:
* Valid for:
 
Post Buying Request Now
close
Remarks: The blank with*must be completed