Trifluoroacetic acid → 7-Amino-3vinyl-3-cephem-4-carboxylic acid

HRID 1154197Notes

Reaction equation

HRID 1154197 reaction equation
C(=[N: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]([CH:17]=[CH2:18])[CH2:15][S:16][C@H:11]12)C1C(=CC=CC=1)O.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>C(Cl)Cl.C1(OC)C=CC=CC=1>[NH2:9][CH:10]1[C:35](=[O:36])[N:12]2[C:13]([C:19]([OH:21])=[O:20])=[C:14]([CH:17]=[CH2:18])[CH2:15][S:16][C@H:11]12

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 136460592Benzhydryl 7-salicylideneamino-3-vinyl-3-cephem-4-carboxylate

Product 1

HCID 128180067-Amino-3vinyl-3-cephem-4-carboxylic acidYield 54.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a solution of benzhydryl 7-salicylideneamino-3-vinyl-3-cephem-4-carboxylate (1.6 g) in methylene chloride (20 ml) and anisole (5 ml) was added dropwise trifluoroacetic acid (6 ml) with stirring, and the stirring was continued at ambient temperature for an hour. The reaction mixture was poured into diisopropyl ether, and the precipitates were collected by filtration and then suspended in water, followed by adjusting to pH 3.5 with a saturated aqueous sodium bicarbonate. The solid was collected by filtration to give 7-amino-3-vinyl-3-cephem-4-carboxylic acid (0.4 g).

Workup

  1. waitthe stirring was continued at ambient temperature for an hour
  2. filtrationthe precipitates were collected by filtration
  3. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-3342a9d4259a4fd094b9d8311e367a86
Source dataset
uspto-grants-1984_12
Patent number
US04487927

Reaction notes

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