Trifluoroacetic acid → HCID 22867252, compound

HRID 1858513Notes

Reaction equation

HRID 1858513 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:42](=[O:43])[N:13]3[C:14]([C:26]([O:28]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:27])=[C:15]([O:18][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>ClCCl.C1(OC)C=CC=CC=1>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:42](=[O:43])[N:13]3[C:14]([C:26]([OH:28])=[O:27])=[C:15]([O:18][S:19]([C:22]([F:24])([F:25])[F:23])(=[O:20])=[O:21])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 11072274HCID 11072274, compound

Product 1

HCID 22867252HCID 22867252, compoundYield 113.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a solution of benzhydryl 7β-(2-phenylacetamido)-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate (9.0 g) in a mixture of dichloromethane (27 ml) and anisole (9 ml) was added trifluoroacetic acid (18 ml) under ice-cooling. The mixture was stirred at the same temperature for 1 hour. The reaction mixture was poured into diisopropyl ether (380 ml) The precipitate was collected by filtration and dried to give 7β-(2-phenylacetamido)-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylic acid (7.55 g).

Workup

  1. temperaturecooling
  2. filtrationwas collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-f72a8e65327942898db02a74f9fbaf0f
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

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