Formic Acid → 3-Acetoxymethyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

HRID 1395330Notes

Reaction equation

HRID 1395330 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:48])[C:19]([C:23]3[N:24]=[C:25]([NH:28]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:26][CH:27]=3)=[N:20][O:21][CH3:22])[C:15](=[O:49])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2].C(O)=O>O>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:48])[C:19]([C:23]3[N:24]=[C:25]([NH2:28])[S:26][CH:27]=3)=[N:20][O:21][CH3:22])[C:15](=[O:49])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 1317115023-Acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 1317115033-Acetoxymethyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acidYield 67.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 0.975 g of the product of Step A and 4 ml of 50% aqueous formic acid was stirred for 10 minutes at 55° C. and after the addition of 4 ml of water, the mixture was vacuum filtered. The filtrate was evaporated under reduced pressure to dryness and the residue was effloresced with 2 ml of ethanol. The mixture was vacuum filtered and the product was washed with ethanol and then ether to obtain 0.428 g of pure 3-acetoxymethyl-7-[{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetyl}amino]-ceph-3-eme-4-carboxylic acid in the syn configuration.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated under reduced pressure to dryness
  3. filtrationfiltered
  4. washthe product was washed with ethanol

Sources & evidence

ORD record
ord-2cfbd6bb47b74e328a7e274f1a606c6a
Source dataset
uspto-grants-1980_05
Patent number
US04202893

Reaction notes

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