64308-63-0

Basic information

• Product Name: GCLH
• Synonyms: 7-PHENYLACETAMIDE-3-CHLOROMETHYL-3-CEPHEM-4-CARBOXYLIC ACID DIPHENYLMETHYL ESTER;7-PHENYLACETAMIDO-3-CHLOROMETHYL-3-CEPHEM-4-CARBOXYLIC ACID DIPHENYL METHYL ESTER;7-PHENYLACETAMIDO-3-CHLOROMETHYL-3-CEPHEM-4-CARBOXYYLIC ACID DIPHENYLMETHYL ESTER;7-PHENYLACETAMINO-3-CHLOROMETHYL-3-CEPHEM4-CARBOXYLIC ACID DIPHENYLMETHYL ESTER;GCLH;GCLH:7-PHENYLACETAMIDO-3-CHLOROMETHYL-3-CEPHEM-4-CARBOXYLIC ACID DIPHENYL METHYL ESTER;3-Cloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Diphenylmethyl Este;7-PHENYLACETAMIDO-3-CHLOROMETHYL-3-CEPHEM-4-CARBOXYLIC ACID
• CAS NO: 64308-63-0
• Molecular Formula: C₂₉H₂₅ClN₂O₄S
• Molecular Weight: 533.04
• Product Categories: Organic acids;Heterocyclic Compounds;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 64308-63-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 85-87°C
• Boiling Point: 778.92 °C at 760 mmHg
• Flash Point: 424.876 °C
• Appearance: Off-white to yellowish crystalline powder
• Density: 1.399 g/cm³
• Vapor Pressure: 3.32E-24mmHg at 25°C
• Refractive Index: 1.685
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly, Heated), Methanol (Slightly, Heated, Sonicated)
• PKA: 13.61±0.60(Predicted)
• CAS DataBase Reference: GCLH(CAS DataBase Reference)
• NIST Chemistry Reference: GCLH(64308-63-0)
• EPA Substance Registry System: GCLH(64308-63-0)

Safety Data

• Hazardous Substances Data: 64308-63-0(Hazardous Substances Data)

Usage

Description

GCLH, also known as Glycerol, is a simple polyol compound that serves as an intermediate in the synthesis of various beta-lactam antibiotics. It is a colorless, odorless, and viscous liquid with a sweet taste. Glycerol is a versatile compound with a wide range of applications across different industries due to its unique properties.

Uses

Used in Pharmaceutical Industry:
GCLH is used as an intermediate in the synthesis of various beta-lactam antibiotics for the development of life-saving medications. Beta-lactam antibiotics are a class of antibiotics that include penicillins, cephalosporins, and carbapenems, which are widely used to treat bacterial infections.
Used in Cosmetics Industry:
GCLH is used as a humectant in cosmetics and personal care products to retain moisture and improve skin hydration. Its hygroscopic nature helps to maintain the skin's natural moisture balance, making it an essential ingredient in various skincare products.
Used in Food Industry:
GCLH is used as a sweetener, emulsifier, and humectant in the food industry. It helps to improve the texture, taste, and shelf life of various food products, such as baked goods, confectionery, and beverages.
Used in Chemical Industry:
GCLH is used as a raw material in the production of various chemicals, such as glycerol esters, glycerol ethers, and glycerol derivatives. These chemicals are used in the manufacturing of various products, including resins, plastics, and solvents.
Used in Energy Industry:
GCLH is used as a feedstock for the production of biofuels, such as biodiesel and biogasoline. It can be converted into renewable energy sources, contributing to a cleaner and more sustainable energy future.

InChI:InChI=1/C29H25ClN2O4S/c30-17-22-18-37-28-24(31-23(33)16-19-10-4-1-5-11-19)27(34)32(28)25(22)29(35)36-26(20-12-6-2-7-13-20)21-14-8-3-9-15-21/h1-15,24,26,28H,16-18H2,(H,31,33)

Synthetic route

(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 (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)

Conditions	Yield
With 2,6-dimethylpyridine; triethylamine In acetonitrile at 0 - 20℃;	97%

(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

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; trifuran-2-yl-phosphane In tetrahydrofuran at 60℃; for 2h;	95%

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)

Conditions	Yield
With trifuran-2-yl-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran for 1h; Heating;	92%

tributyl(thien-2-yl)stannane (54663-78-4) + (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)-8-Oxo-7-phenylacetylamino-3-thiophen-2-ylmethyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (36242-69-0)

Conditions	Yield
With trifuran-2-yl-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran for 2.5h; Heating;	87%

(p-methoxyphenyl)tri-n-butylstannane (70744-47-7) + (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)-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 (36242-67-8)

Conditions	Yield
With trifuran-2-yl-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran for 24h; Heating;	81%

(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) + 6-Tributylstannyl-2',3'-isopropylidene-5'-O-methoxymethyluridine → 3-<(2',3'-Isopropylidene-5'-O-methoxymethyl)uridin-6-yl>methyl-8-oxo-7-<(phenylacetyl)amino>-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester

Conditions	Yield
With copper(l) iodide; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran at 60℃; for 0.5h;	79%

(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)-8-Oxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (609812-88-6)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaI / acetone / 1 h / 20 °C 2.1: 0.715 g / ethyl acetate / 12 h 3.1: aq. NaOH / CH2Cl2 / 0.5 h / 20 °C 3.2: 28 percent / CH2Cl2 / 20 °C 4.1: 71 percent / TFA / CH2Cl2; methoxybenzene / 1 h / 0 °C View Scheme

(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) → (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (852671-27-3)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: NaI / acetone / 1 h / 20 °C 2.1: 0.715 g / ethyl acetate / 12 h 3.1: aq. NaOH / CH2Cl2 / 0.5 h / 20 °C 3.2: 28 percent / CH2Cl2 / 20 °C 4.1: m-CPBA / CH2Cl2 / 0.33 h 5.1: 16.71 mg / TFA / CH2Cl2; methoxybenzene / 1 h / 0 °C View Scheme

(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)-8-Oxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (609812-77-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: NaI / acetone / 1 h / 20 °C 2.1: 0.715 g / ethyl acetate / 12 h 3.1: aq. NaOH / CH2Cl2 / 0.5 h / 20 °C 3.2: 28 percent / CH2Cl2 / 20 °C View Scheme

(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) → (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (852671-30-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaI / acetone / 1 h / 20 °C 2.1: 0.715 g / ethyl acetate / 12 h 3.1: aq. NaOH / CH2Cl2 / 0.5 h / 20 °C 3.2: 28 percent / CH2Cl2 / 20 °C 4.1: m-CPBA / CH2Cl2 / 0.33 h View Scheme

(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)-7t-amino-8-oxo-3-thiophen-2-ylmethyl-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (54493-78-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / tri(2-furyl)phosphine / bis(dibenzylideneacetonyl)palladium / tetrahydrofuran / 2.5 h / Heating 2: 1.) PCl5, 2.) 1,3-propanediol / 1.) pyridine View Scheme

(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)-7-Amino-3-furan-2-ylmethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / tri(2-furyl)phosphine / bis(dibenzylideneacetonyl)palladium / tetrahydrofuran / 1 h / Heating 2: 1.) PCl5, 2.) 1,3-propanediol / 1.) pyridine View Scheme

(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)-7-Amino-8-oxo-3-thiazol-5-ylmethyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (1051930-92-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 30 percent / tri(2-furyl)phosphine / bis(dibenzylideneacetonyl)palladium / tetrahydrofuran / 24 h / Heating 2: 1.) PCl5, 2.) 1,3-propanediol / 1.) pyridine View Scheme

(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)-7-Amino-3-(3-methyl-isoxazol-5-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 56 percent / tri(2-furyl)phosphine / bis(dibenzylideneacetonyl)palladium / tetrahydrofuran / 14 h / Heating 2: 1.) PCl5, 2.) 1,3-propanediol / 1.) pyridine View Scheme

(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)-7-Amino-3-(2-methylsulfanyl-thiazol-5-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (1060672-84-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / tri(2-furyl)phosphine / bis(dibenzylideneacetonyl)palladium / tetrahydrofuran / 10 h / Heating 2: 1.) PCl5, 2.) 1,3-propanediol / 1.) pyridine View Scheme

(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-(2-Acetyl-thiazol-5-ylmethyl)-7-amino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (1058141-95-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 61 percent / tri(2-furyl)phosphine / bis(dibenzylideneacetonyl)palladium / tetrahydrofuran / 19 h / Heating 2: 1.) PCl5, 2.) 1,3-propandiol / 1.) pyridine View Scheme

(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)-7-Amino-3-(5-methoxycarbonyl-thiophen-2-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / tri(2-furyl)phosphine / bis(dibenzylideneacetonyl)palladium / tetrahydrofuran / 5 h / Heating 2: 1.) PCl5, 2.) 1,3-propanediol / 1.) pyridine View Scheme

(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)-7-Amino-8-oxo-3-(2-phenylsulfanyl-thiazol-5-ylmethyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (1060646-17-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / tri(2-furyl)phosphine / bis(dibenzylideneacetonyl)palladium / tetrahydrofuran / 5 h / Heating 2: 1.) PCl5, 2.) 1,3-propanediol / 1.) pyridine View Scheme

(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)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-3-thiophen-2-ylmethyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / tri(2-furyl)phosphine / bis(dibenzylideneacetonyl)palladium / tetrahydrofuran / 2.5 h / Heating 2: 1.) PCl5, 2.) 1,3-propanediol / 1.) pyridine 3: CH2Cl2 View Scheme

(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)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-furan-2-ylmethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / tri(2-furyl)phosphine / bis(dibenzylideneacetonyl)palladium / tetrahydrofuran / 1 h / Heating 2: 1.) PCl5, 2.) 1,3-propanediol / 1.) pyridine 3: CH2Cl2 View Scheme

(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)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-3-thiazol-5-ylmethyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (1062608-07-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 30 percent / tri(2-furyl)phosphine / bis(dibenzylideneacetonyl)palladium / tetrahydrofuran / 24 h / Heating 2: 1.) PCl5, 2.) 1,3-propanediol / 1.) pyridine 3: CH2Cl2 View Scheme

Upstream product

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

Downstream Products

• 36242-67-8 (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 
• 36242-67-8 (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 
• 36242-70-3 (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 
• 36242-69-0 (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 
• 157025-23-5 (6R,7R)-3-(3-Methyl-isoxazol-5-ylmethyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 157025-18-8 (6R,7R)-8-Oxo-7-phenylacetylamino-3-thiazol-5-ylmethyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 157025-19-9 (6R,7R)-3-(2-Methylsulfanyl-thiazol-5-ylmethyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 157025-21-3 (6R,7R)-3-(2-Acetyl-thiazol-5-ylmethyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 157025-17-7 (6R,7R)-3-(5-Methoxycarbonyl-thiophen-2-ylmethyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 157025-20-2 (6R,7R)-8-Oxo-7-phenylacetylamino-3-(2-phenylsulfanyl-thiazol-5-ylmethyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 51761-83-2 (6R,7R)-benzhydryl 3-(iodomethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 1262837-61-5 (6R,7R)-8-oxo-3-(((2-oxo-2H-chromen-7-yl)oxy)methyl)-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 

Relevant articles and documents

BETA-LACTAMASE SUBSTRATES AND METHODS OF THEIR USE FOR THE DIAGNOSIS OF TUBERCULOSIS

β-Lactamase substrates and methods for using the substrates to detect β-lactamase diagnose tuberculosis.