GCLH

Base Information

• Chemical Name: GCLH
• CAS No.: 64308-63-0
• Molecular Formula: C29H25ClN2O4S
• Molecular Weight: 533.048
• Mol file: 64308-63-0.mol

Synonyms:5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 3-(chloromethyl)-8-oxo-7-[(phenylacetyl)amino]-, diphenylmethyl ester,(6R,7R)- (9CI);5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-(chloromethyl)-8-oxo-7-[(phenylacetyl)amino]-, diphenylmethyl ester, (6R-trans)-;7-Phenylacetamido-3-(chloromethyl)-3-cephem-4-carboxylic acid diphenylmethylester;

Chemical Property of GCLH

Chemical Property:

• Appearance/Colour: Off-white to yellowish crystalline powder
• Vapor Pressure: 3.32E-24mmHg at 25°C
• Melting Point: 85-87 °C
• Refractive Index: 1.685
• Boiling Point: 778.92 °C at 760 mmHg
• PKA: 13.61±0.60(Predicted)
• Flash Point: 424.876 °C
• PSA: 101.01000
• Density: 1.399 g/cm³
• LogP: 4.78350
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly, Heated), Methanol (Slightly, Heated, Sonicated)

Purity/Quality:

99% ^*data from raw suppliers

7-Phenylacetamide-3-chloromethyl-3-cephem-4-carboxylic acid diphenylmethyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate in the synthesis of various beta-lactam antibiotics An intermediate in the synthesis of various beta-lactam antibiotics.

Technology Process of GCLH

There total 1 articles about GCLH 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: 97.0%

(6R,7R)-7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxyli acid diphenylmethyl ester hydrochloride (79349-53-4) + phenylacetyl chloride (103-80-0) → (6R,7R)-benzhydryl 3-(chloromethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (64308-63-0)

Guidance literature:

With 2,6-dimethylpyridine; triethylamine; In acetonitrile; at 0 - 20 ℃;

Reference yield: 95.0%

(6R,7R)-benzhydryl 3-(chloromethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (64308-63-0) + 2-(tributylstannyl)-1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-indole (153432-70-3) → diphenylmethyl 8-oxo-7-<(phenylacetyl)amino>-3-<<1'-<<2-(trimethylsilyl)ethoxy>methyl>-1'H-indol-2'-yl>methyl>-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; trifuran-2-yl-phosphane; In tetrahydrofuran; at 60 ℃; for 2h;

DOI:10.1002/hlca.19930760622

Reference yield: 92.0%

2-(tributylstannyl)furan (118486-94-5) + (6R,7R)-benzhydryl 3-(chloromethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (64308-63-0) → (6R,7R)-3-Furan-2-ylmethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (36242-70-3)

Guidance literature:

With trifuran-2-yl-phosphane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; for 1h; Heating;

DOI:10.7164/antibiotics.47.606

upstream raw materials:

(6R,7R)-7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxyli acid diphenylmethyl ester hydrochloride

phenylacetyl chloride

Downstream raw materials:

(6R,7R)-3-(4-Methoxy-benzyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

(6R)-3-(4-methoxy-benzyl)-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

(6R,7R)-3-Furan-2-ylmethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

(6R,7R)-8-Oxo-7-phenylacetylamino-3-thiophen-2-ylmethyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Refernces