Pivaloyloxymethyl 3-azidomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(1-methyl-1-methoxy-ethoxyimino)-acetamido]-ceph-3-eme-4-carboxylate → Pivaloyloxymethyl 3-azidomethyl-7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylate

HRID 904918Notes

Reaction equation

HRID 904918 reaction equation
[N:1]([CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:23]([NH:24][C:25](=[O:59])[C:26]([C:34]3[N:35]=[C:36]([NH:39]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:37][CH:38]=3)=[N:27][O:28]C(C)(OC)C)[C:22](=[O:60])[N:9]2[C:10]=1[C:11]([O:13][CH2:14][O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:12])=[N+:2]=[N-:3]>C(O)=O>[N:1]([CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:23]([NH:24][C:25](=[O:59])[C:26]([C:34]3[N:35]=[C:36]([NH2:39])[S:37][CH:38]=3)=[N:27][OH:28])[C:22](=[O:60])[N:9]2[C:10]=1[C:11]([O:13][CH2:14][O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:12])=[N+:2]=[N-:3]

Participants

3

Reactant 1

HCID 131713257Pivaloyloxymethyl 3-azidomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(1-methyl-1-methoxy-ethoxyimino)-acetamido]-ceph-3-eme-4-carboxylate

Product 1

HCID 131713258Pivaloyloxymethyl 3-azidomethyl-7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylateYield 44.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

A mixture of 753 mg of the product of Step B, 0.75 ml of 98% formic acid and 9.25 ml of 50% aqueous formic acid was stirred at 55°-60° C. for 12 minutes and the mixture was evaporated to dryness at a temperature not above 30° C. The residue was taken up in 5 ml of water and the mixture was vacuum filtered. The product was washed with water and then with isopropyl ether and dried. The 481 mg of product was chromatographed over silica gel and was eluted with a 1-1 acetone-methylene chloride mixture to obtain 211 mg of the pivaloyloxymethyl 3-azidomethyl-7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylate.

Workup

  1. customthe mixture was evaporated to dryness at a temperature not above 30° C
  2. filtrationfiltered
  3. washThe product was washed with water
  4. dry with materialwith isopropyl ether and dried
  5. customThe 481 mg of product was chromatographed over silica gel
  6. washwas eluted with a 1-1 acetone-methylene chloride mixture

Sources & evidence

ORD record
ord-1cfc1207b0574aeab51e34f8badb796c
Source dataset
uspto-grants-1983_12
Patent number
US04420478

Reaction notes

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