Trifluoroacetic acid → HCID 178510676, compound

HRID 1858517Notes

Reaction equation

HRID 1858517 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:48](=[O:49])[N:13]3[C:14]([C:32]([O:34]C(C4C=CC=CC=4)C4C=CC=CC=4)=[S:33])=[C:15]([C:18]4[S:19][C:20]([CH2:23][NH:24]C(OC(C)(C)C)=O)=[N:21][N:22]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53].C(OC(C)C)(C)C>ClCCl.C1(OC)C=CC=CC=1>[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53].[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:48](=[O:49])[N:13]3[C:14]([C:32]([OH:34])=[S:33])=[C:15]([C:18]4[S:19][C:20]([CH2:23][NH2:24])=[N:21][N:22]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131722168HCID 131722168, compound

Product 1

HCID 178510676HCID 178510676, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a solution of benzhydryl 7β-(2-phenylacetamido)-3-(5-tert-butoxycarbonylaminomethyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate (683 mg) in a mixture of dichloromethane (2.1 ml) and anisole (0.7 ml) was added trifluoroacetic acid (1.4 ml) under ice-cooling. The mixture was stirred at the same temperature for 30 minutes and at room temperature for 3 hours. The reaction mixture was poured into diisopropyl ether (70 ml). The precipitate was collected by filtration and dried over to give 7β-(2-phenylacetamido)-3-(5-aminomethyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylic acid trifluoroacetic acid salt (525 mg).

Workup

  1. temperaturecooling
  2. filtrationThe precipitate was collected by filtration
  3. customdried over

Sources & evidence

ORD record
ord-878418f1773d40f39dbf2d1230296864
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

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