Sulfuric Acid → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

HRID 1087261Notes

Reaction equation

HRID 1087261 reaction equation
ClCCl.C[C:5]([O:7][CH2:8][C:9]1[CH2:18][S:17][C@@H:12]2[C@H:13]([NH2:16])[C:14](=[O:15])[N:11]2[C:10]=1[C:19]([OH:21])=[O:20])=O.S(=O)(=O)(O)O>CO>[NH2:16][CH:13]1[C:14](=[O:15])[N:11]2[C:10]([C:19]([OH:21])=[O:20])=[C:9]([CH2:8][O:7][CH3:5])[CH2:18][S:17][C@H:12]12

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 128330237-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 10 ml of dichloromethane were added 1.41 g of 7-ACA, 2.1 ml of concentrated sulfuric acid and 1.05 ml of methanol. The reaction was conducted at 0° C. for 1.75 hours. After completion of the reaction, substantially the same procedure as in Example 1 was repeated, to thereby obtain the desired product, namely 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid. The amount of the desired product was 0.27 g. The yield of the desired product was 21%.

Workup

  1. customAfter completion of the reaction

Sources & evidence

ORD record
ord-6b6bac9a334c4978815c5400bc27f059
Source dataset
uspto-grants-1991_07
Patent number
US05034521

Reaction notes

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