Trifluoroacetic acid → HCID 131710934, compound

HRID 972495Notes

Reaction equation

HRID 972495 reaction equation
C1(C(C2C=CC=CC=2)[O:8][C:9]([CH2:11][O:12][N:13]=[CH:14][C:15]2[CH2:16][S:17][C@@H:18]3[CH:38]([NH:39][C:40](=[O:47])[CH2:41][C:42]4[S:43][CH:44]=[CH:45][CH:46]=4)[C:37](=[O:48])[N:19]3[C:20]=2[C:21]([O:23]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:22])=[O:10])C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:9]([CH2:11][O:12][N:13]=[CH:14][C:15]1[CH2:16][S:17][C@@H:18]2[CH:38]([NH:39][C:40](=[O:47])[CH2:41][C:42]3[S:43][CH:44]=[CH:45][CH:46]=3)[C:37](=[O:48])[N:19]2[C:20]=1[C:21]([OH:23])=[O:22])([OH:10])=[O:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131710935HCID 131710935, compound

Product 1

HCID 131710934HCID 131710934, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diphenylmethyl 3-(diphenylmethoxycarbonylmethoxyiminomethyl)-7-(2-thienylacetamido)-3-cephem-4-carboxylate (187 mg) in methylene chloride (4 ml) are added anisole (0.8 ml) at 0° C., and trifluoroacetic acid (0.8 ml) under argon atmosphere, and the mixture is stirred for 10 minutes at room temperature. After evaporation of the methylene chloride and trifluoroacetic acid, the mixture is treated with ether to give 3-(carboxymethoxyiminomethyl)-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid (86 mg). m.p. 158°-163° C. (decomp.).

Workup

  1. customAfter evaporation of the methylene chloride and trifluoroacetic acid
  2. additionthe mixture is treated with ether

Sources & evidence

ORD record
ord-86f453eb65d74360885ac594168fafb0
Source dataset
uspto-grants-1977_10
Patent number
US04053469

Reaction notes

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