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(6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid structure

CAS No:
15690-38-7
Formula:
C8H10N2O4S
Chemical Name:
(6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Synonyms:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-amino-3-(hydroxymethyl)-8-oxo-,(6R,7R)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-amino-3-(hydroxymethyl)-8-oxo-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-amino-3-(hydroxymethyl)-8-oxo-,(6R-trans)-;(6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;7-Amino-3-hydroxymethyl-3-cephem-4-carboxylic acid;(6R,7R)-7-Amino-3-hydroxymethylceph-3-em-4-carboxylic acid;3-Hydroxymethyl-7-aminoceph-3-em-4-carboxylic acid;Deacetyl-7-aminocephalosporanic acid;7β-Amino-3-(hydroxymethyl)-3-cephem-4-carboxylic acid;7-Amino-deacetylcephalosporanic acid;856323-62-1;1447717-05-6
Categories:
Active Pharmaceutical Ingredients > Antibiotics

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Description

Beige Solid

(6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Basic Attributes

Molecular Weight：

302.30366

Exact Mass：

230.24

EC Number：

239-787-2

Characteristics

PSA：

129

XLogP3：

-4.6

Density：

1.74

Boiling Point：

617.9±55.0 °C(Predicted)

Flash Point：

327.5±31.5 °C

Refractive Index：

1.743

Vapor Pressure：

7.46E-18mmHg at 25°C

Safety Information

Precautionary statement(s)：

P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, P501

Hazard Statements：

H317

(6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Use and Manufacturing

Methods of Manufacturing

Weigh 7-ACA 27.2g (0.1mol), Add 50mL of methanol and 50mL of water, Add 3.0g tetra-n-butane at -5-5°CAmmonium chloride stirring to dissolve, Maintain the addition of 2mol/L sodium hydroxide solution 105mL at this temperature.After dripping, maintain the temperature and continue stirring for 0.5-1 hour.Then add 30percent hydrochloric acid to adjust the pH to neutral, Precipitation of solids, suction filtration, anhydrous ethanol washing, 20.7g of dried white solidYield 90.1percent, HPLC purity analysis 97.35percent (area normalization method), Lactone impurity 0.33percent.In the first step: 20 g of 7-ACA was added to a solution consisting of 140 mL of methanol and 140 mL of water, cooled to -10 to -20 ° C, 15.6 mL of a 10 mol / L NaOH solution was added dropwise, stirred for 10 min, The reaction solution was slowly neutralized with 1 mol / L HCl solution to pH to pH 3. After filtration, the filter cake was washed successively with methanol, acetone and diethyl ether and dried in vacuo to give 14.5 g White 7-AHCA, the yield was 86percent;In a 1000ml reaction bottle, Add D-7-ACA40.0g, 100 g of cefixime active ester, 380 ml of THF (tetrahydrofuran), and 355 ml of pure water were added.The temperature was controlled to 0 to 30 C under stirring, and 60 ml of THF + 40 ml of TEA (triethylamine) was slowly added dropwise.The temperature was maintained for about 2 hours, and the temperature was maintained for 10 hours after the addition.HPLC detection of D-7-ACA residues below 0.5% of the reaction is complete.Extracted twice with 550 ml of ethyl acetate, and the ethyl acetate phase was recovered after extraction.The aqueous phase was adjusted to pH 3.6-3.7 with 9% dilute hydrochloric acid, and filtered.Drying gave about 80.9 g of the first intermediate

Uses

Intermediate in the semi-synthetic cephalosporins synthesis. Found in Acremonium chrysogenum.

Price Analysis

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CAS No.: 15690-38-7

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CAS No.: 15690-38-7

Grade: Pharmaceutical Grade

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Guide of (6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Description
Basic Attributes
Characteristics
Safety Information
Use and Manufacturing
Price Analysis
Recommended Suppliers
Latest News
Learn More Other Chemicals

(6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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