Formic acid--water (1/1) → 3-Azidomethyl-7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

HRID 904914Notes

Reaction equation

HRID 904914 reaction equation
[N:1]([CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:15]([NH:16][C:17](=[O:46])[C:18]([C:21]3[N:22]=[C:23]([NH:26]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:24][CH:25]=3)=[N:19][OH:20])[C:14](=[O:47])[N:9]2[C:10]=1[C:11]([OH:13])=[O:12])=[N+:2]=[N-:3].C(O)=O.O>O>[N:1]([CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:15]([NH:16][C:17](=[O:46])[C:18]([C:21]3[N:22]=[C:23]([NH2:26])[S:24][CH:25]=3)=[N:19][OH:20])[C:14](=[O:47])[N:9]2[C:10]=1[C:11]([OH:13])=[O:12])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 18673298Formic acid--water (1/1)HCID 1317132513-Azidomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

Product 1

HCID 1317132533-Azidomethyl-7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the product of Step B and 6 ml of 2-1 formic acid-water mixture was stirred at 45°-50° C. was stirred for 10 minutes and was diluted with 7 ml of water. The mixture was vacuum filtered and the filtrate was evaporated to dryness. The residue was added all at once to 10 ml of water and the mixture was triturated and vacuum filtered to obtain 0.95 g of the raw syn isomer of 3-azidomethyl-7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylic acid.

Workup

  1. stirringwas stirred for 10 minutes
  2. filtrationfiltered
  3. customthe filtrate was evaporated to dryness
  4. additionThe residue was added all at once to 10 ml of water
  5. customthe mixture was triturated
  6. filtrationvacuum filtered

Sources & evidence

ORD record
ord-7657e65cde64423f86d136aa77d94ab3
Source dataset
uspto-grants-1983_12
Patent number
US04420478

Reaction notes

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