Trifluoroacetic acid → HCID 178525676, compound

HRID 2412465Notes

Reaction equation

HRID 2412465 reaction equation
C(OC[C:6]1[CH2:7][S:8][C@@H:9]2[CH:29]([NH:30][C:31]3[NH:32][CH:33]=[C:34]([CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[N:35]=3)[C:28](=[O:43])[N:10]2[C:11]=1[C:12]([O:14]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:13])(=O)C.[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]>C1(OC)C=CC=CC=1>[F:47][C:46]([F:49])([F:48])[C:44]([OH:50])=[O:45].[CH2:36]([C:34]1[N:35]=[C:31]([NH:30][CH:29]2[C:28](=[O:43])[N:10]3[C:11]([C:12]([OH:14])=[O:13])=[CH:6][CH2:7][S:8][C@H:9]23)[NH:32][CH:33]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178475880HCID 178475880, compound

Product 1

HCID 178525676HCID 178525676, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

A solution of diphenylmethyl 3-acetoxymethyl-7-(4-benzylimidazol-2-yl)aminoceph-3-em-4-carboxylate (106 mg.) in a mixture of anisole (0.7 ml.) and TFA (0.4 ml.) was stirred at ambient temperature for 30 minutes and then evaporated to dryness at 25°. The residue was dissolved in the minimum amount of methylene chloride and precipitated with hexane to give 7-(4-benzylimidazol-2-yl)aminoceph-3-em-4-carboxylic acid trifluoroacetate (61 mg.), m.p. 200°-220°, having the following n.m.r. spectrum in d6DMSO: 2.0 (s, 3H); 3.6 (s, 2H); 3.9 (s, 2H); 4.7 (d, 1H); 5.0 (d, 1H); 5.2 (d, 1H); 5.6 (dd, 1H); 6.8 (s, 1H); 7.3 (s, 5H); 9.3 (d, 1H).

Workup

  1. customevaporated to dryness at 25°
  2. dissolutionThe residue was dissolved in the minimum amount of methylene chloride
  3. customprecipitated with hexane

Sources & evidence

ORD record
ord-11ef2b5f56814e6d8f5b64d5462cb8c6
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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