Trifluoroacetic acid → HCID 178501867, compound

HRID 1262773Notes

Reaction equation

HRID 1262773 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:37][O:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])[C:8]([NH:10][CH:11]2[C:35](=[O:36])[N:13]3[C:14]([C:19]([O:21]C(C4C=CC=CC=4)C4C=CC=CC=4)=[S:20])=[C:15]([CH3:18])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>ClCCl>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:37][O:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])[C:8]([NH:10][CH:11]2[C:35](=[O:36])[N:13]3[C:14]([C:19]([OH:21])=[S:20])=[C:15]([CH3:18])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 131713542HCID 131713542, compound

Product 1

HCID 178501867HCID 178501867, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-(methoxycarbonylmethoxyimino)acetamido]-3-methylthio-3-cephem-4-carboxylate (syn isomer) (11.6 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 2 hours. The reaction mixture was dropwise added to isopropyl ether (200 ml) under stirring and the precipitates were collected by filtration. The precipitates were dissolved in ethyl acetate and saturated sodium bicarbonate solution and aqueous layer was separated. The aqueous layer was adjusted to pH 4.5 with 10% hydrochloric acid. After removing the solvent in reduced pressure, the solution was acidified to pH 2.5 with 10% hydrochloric acid under ice-cooling. The precipitates were filtered and dried to give 7-[2-(2-aminothiazol-4-yl)-2-(methoxycarbonylmethoxyimino)acetamido]-3-methylthio-3-cephem-4-carboxylic acid (syn isomer) (6.1 g).

Workup

  1. temperaturecooling
  2. stirringunder stirring
  3. filtrationthe precipitates were collected by filtration
  4. dissolutionThe precipitates were dissolved in ethyl acetate
  5. customsaturated sodium bicarbonate solution and aqueous layer was separated
  6. customAfter removing the solvent in reduced pressure
  7. temperaturecooling
  8. filtrationThe precipitates were filtered
  9. customdried

Sources & evidence

ORD record
ord-47f04f2a542445e090ebf96b076c743b
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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