7-[2-(2-formamidothiazol-4-yl)-2-(2-azidoethoxyimino)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid → 7-[2-(2-formamidothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 255763Notes

Reaction equation

HRID 255763 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:33][O:34][CH2:35][CH2:36][N:37]=[N+]=[N-])[C:10]([NH:12][CH:13]2[C:31](=[O:32])[N:15]3[C:16]([C:28]([OH:30])=[O:29])=[C:17]([CH2:20][S:21][C:22]4[N:26]([CH3:27])[N:25]=[N:24][N:23]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]>[C].[Pd].C(O)(=O)C>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:33][O:34][CH2:35][CH2:36][NH2:37])[C:10]([NH:12][CH:13]2[C:31](=[O:32])[N:15]3[C:16]([C:28]([OH:30])=[O:29])=[C:17]([CH2:20][S:21][C:22]4[N:26]([CH3:27])[N:25]=[N:24][N:23]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]

Participants

4

Reactant 1

HCID 1317152897-[2-(2-formamidothiazol-4-yl)-2-(2-azidoethoxyimino)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317152907-[2-(2-formamidothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidYield 52.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-(2-azidoethoxyimino)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 0.70 g.), 10% palladium carbon (0.85 g.) and acetic acid (10 ml.) was subjected to catalytic reduction under ordinary pressure at room temperature for 13 hours. The resultant mixture was filtered, and the filtrate was concentrated in vacuo. The residue was stirred in diisopropyl ether (30 ml.) and methanol (10 ml.) for an hour. The precipitates were collected by filtration, washed with diisopropyl ether and dried to give 7-[2-(2-formamidothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 0.35 g.).

Workup

  1. filtrationThe resultant mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. waitmethanol (10 ml.) for an hour
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with diisopropyl ether
  6. customdried

Sources & evidence

ORD record
ord-a7dce2ca1fbe47a3b19c2204e71901be
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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