Trifluoroacetic acid → 7-Benzoylamino-3-chloromethyl-3-cephem-4-carboxylic acid

HRID 1607943Notes

Reaction equation

HRID 1607943 reaction equation
[C:1]([NH:9][CH:10]1[C:35](=[O:36])[N:12]2[C:13]([C:19]([O:21]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:20])=[C:14]([CH2:17][Cl:18])[CH2:15][S:16][C@H:11]12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C.CCCCCC>ClCCl.C1(OC)C=CC=CC=1>[C:1]([NH:9][CH:10]1[C:35](=[O:36])[N:12]2[C:13]([C:19]([OH:21])=[O:20])=[C:14]([CH2:17][Cl:18])[CH2:15][S:16][C@H:11]12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 8058HexaneHCID 67834587Benzhydryl 7-benzoylamino-3-chloromethyl-3-cephem-4-carboxylate

Product 1

HCID 678346777-Benzoylamino-3-chloromethyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a solution of benzhydryl 7-benzoylamino-3-chloromethyl-3-cephem-4-carboxylate (20 g) in a mixture of dichloromethane (40 ml) and anisole (10 ml) was added trifluoroacetic acid (20 ml) under cooling. After being stirred for two hours at -3°~0° C., the mixture was added dropwise to a mixture of diisopropyl ether (400 ml) and n-hexan (800 ml) at 5° C. The stirring was continued for 15 minutes at the same temperature. The resulting powder was collected by filtration, washed with n-hexan and dried over phosphorus pentoxide to give 7-benzoylamino-3-chloromethyl-3-cephem-4-carboxylic acid.

Workup

  1. temperatureunder cooling
  2. waitThe stirring was continued for 15 minutes at the same temperature
  3. filtrationThe resulting powder was collected by filtration
  4. washwashed with n-hexan
  5. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-0b2e1cfb68a548bfae26c0ea761ab83b
Source dataset
uspto-grants-1989_09
Patent number
US04868174

Reaction notes

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