Trifluoroacetic acid → HCID 131712318, compound

HRID 745387Notes

Reaction equation

HRID 745387 reaction equation
FC(F)(F)C(O)=O.[CH:8]([NH:10][C:11]1[S:12][CH:13]=[C:14]([C:16](=[N:42][O:43][CH2:44][C:45]([O:47]C(C)(C)C)=[O:46])[C:17]([NH:19][CH:20]2[C:40](=[O:41])[N:22]3[C:23]([C:27]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=4)=[O:28])=[CH:24][CH2:25][S:26][C@H:21]23)=[O:18])[N:15]=1)=[O:9]>C1(OC)C=CC=CC=1>[CH:8]([NH:10][C:11]1[S:12][CH:13]=[C:14]([C:16](=[N:42][O:43][CH2:44][C:45]([OH:47])=[O:46])[C:17]([NH:19][CH:20]2[C:40](=[O:41])[N:22]3[C:23]([C:27]([O:29][CH2:30][C:31]4[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=4)=[O:28])=[CH:24][CH2:25][S:26][C@H:21]23)=[O:18])[N:15]=1)=[O:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131712317HCID 131712317, compound

Product 1

HCID 131712318HCID 131712318, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (40 ml.) was added to a suspension of 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-t-butoxycarbonylmethoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 10 g.) in anisole (10 ml.) at 5° C., and stirred at room temperature for 70 minutes. After evaporating the solvent from the resultant mixture in vacuo, the residue was triturated with diethyl ether. The precipitates were collected by filtration and dried to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 8.2 g.).

Workup

  1. customAfter evaporating the solvent from the resultant mixture in vacuo
  2. customthe residue was triturated with diethyl ether
  3. filtrationThe precipitates were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-e246fc6a07f144a88c82fbeca04f3d2c
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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