Trifluoroacetic acid → HCID 178501866, compound

HRID 1262750Notes

Reaction equation

HRID 1262750 reaction equation
[Cl:1][CH2:2][C:3](=[O:41])[C:4](=[N:34][O:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])[C:5]([NH:7][CH:8]1[C:32](=[O:33])[N:10]2[C:11]([C:16]([O:18]C(C3C=CC=CC=3)C3C=CC=CC=3)=[S:17])=[C:12]([CH3:15])[CH2:13][S:14][C@H:9]12)=[O:6].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>ClCCl.CCCCCC>[Cl:1][CH2:2][C:3](=[O:41])[C:4](=[N:34][O:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])[C:5]([NH:7][CH:8]1[C:32](=[O:33])[N:10]2[C:11]([C:16]([OH:18])=[S:17])=[C:12]([CH3:15])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 131713527HCID 131713527, compound

Product 1

HCID 178501866HCID 178501866, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of benzhydryl 7-[4-chloro-2-methoxycarbonylmethoxyimino-3-oxobutyramido]-3-methylthio-3-cephem-4-carboxylate (syn isomer) (12.65 g) and anisole (8.5 g) in dichloromethane (30 ml) was added trifluoroacetic acid (36.5 g) under ice-cooling and the mixture was stirred at ambient temperature for 1.5 hours. The reaction mixture was dropwise added to a mixture of isopropyl ether and n-hexane (1:1 400 ml) under stirring. The precipitates were collected by filtration and washed with n-hexane to give 7-[4-chloro-2-methoxycarbonylmethoxyimino-3-oxobutyramido]-3-methylthio-3-cephem-4-carboxylic acid (syn isomer) (7.3 g).

Workup

  1. temperaturecooling
  2. stirringunder stirring
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with n-hexane

Sources & evidence

ORD record
ord-954d3aaf828543ff8dfa43c77909eb8d
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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