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

HRID 1195524Notes

Reaction equation

HRID 1195524 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 548.7%

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 (4.0 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-5b18c90da9964a0ca30272493a084a89
Source dataset
uspto-grants-1992_05
Patent number
US05110921

Reaction notes

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