Chloromethyl (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate 4,4-dioxide

Base Information

• Chemical Name: Chloromethyl (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate 4,4-dioxide
• CAS No.: 76247-40-0
• Molecular Formula: C9H12 Cl N O5 S
• Molecular Weight: 281.717
• European Community (EC) Number: 278-401-7
• DSSTox Substance ID: DTXSID60227115
• Nikkaji Number: J1.552.159G,J342.593B
• Wikidata: Q83106763
• Mol file: 76247-40-0.mol

Synonyms:76247-40-0;Chloromethyl (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate 4,4-dioxide;EINECS 278-401-7;chloromethyl (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;CHLOROMETHYL (2S-CIS)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLATE 4,4-DIOXIDE;Chloromethylpenicillanate-1,1-dioxide;C9H12ClNO5S;SCHEMBL6421634;C9-H12-Cl-N-O5-S;DTXSID60227115;(2S,5R)-2-[(Chloromethoxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4,4-dioxide;(2S,5R)-3,3-Dimethyl-4,4,7-trioxo-4-thia(VI)-1-azabicyclo[3.2.0]heptane-2-carboxylic acid chloromethyl ester

Chemical Property of Chloromethyl (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate 4,4-dioxide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 491.258°C at 760 mmHg
• Flash Point: 250.904°C
• PSA: 89.13000
• Density: 1.565g/cm³
• LogP: 0.87860
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 281.0124714
• Heavy Atom Count: 17
• Complexity: 480

Purity/Quality:

98%min ^*data from raw suppliers

CHLOROMETHYL PENICILLANATE-1,1-DIOXIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1(=O)=O)CC2=O)C(=O)OCCl)C
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)OCCl)C

Technology Process of Chloromethyl (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate 4,4-dioxide

There total 14 articles about Chloromethyl (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate 4,4-dioxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.6%

chlorobromomethane (74-97-5) + sulbactum (68373-14-8,1217600-46-8) → chloromethyl penicillanate 1,1-dioxide (76247-40-0)

Guidance literature:

With pyridine; at 20 ℃; for 3.5h; Darkness;

Reference yield: 81.5%

manganese (7439-96-5) + chloromethyl 6,6-dibromopenicillanate 1,1-dioxide (84458-09-3) + cobalt (7440-48-4) → chloromethyl penicillanate 1,1-dioxide (76247-40-0)

Guidance literature:

With iron; In water; acetic acid; ethyl acetate;

Reference yield: 80.0%

chlorosulfuric acid chloromethyl ester (49715-04-0) + sulbactum (68373-14-8,1217600-46-8) → chloromethyl penicillanate 1,1-dioxide (76247-40-0)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; In dichloromethane; 1.) 20-22 deg C, 2.) 30 min;

upstream raw materials:

chlorosulfuric acid chloromethyl ester

sulbactum

manganese

chloromethyl 6,6-dibromopenicillanate 1,1-dioxide

Downstream raw materials:

iodomethyl penicillanate 1,1-dioxide

6'-(2,2-dimethyl-4-phenyl-5-imidazolidinon-1-yl)-penicillanoyloxymethyl penicillanate 1,1-dioxide

6'-(2-Benzyloxycarbonylamino-2-phenylacetamido)-penicillanoyloxymethyl Penicillanate 1,1-Dioxide

6'-(2-[4-Nitrobenzyloxycarbonylamino]-2phenylacetamido)penicillanoyloxymethyl penicillanate 1,1-dioxide

Refernces

• 1、 -. "Procedure for the preparation of dioxopenicillanic acid derivatives". . . Retrieved 2008/06/13.
• 2、 -. "Antibacterial 6'-(2-amino-2-[4-acyloxyphenyl]acetamido)penicillanoyloxymethyl penicillanate 1,1-dioxide compounds". . . Retrieved 2008/06/13.