Trifluoroacetic acid → HCID 131713348, compound

HRID 569441Notes

Reaction equation

HRID 569441 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:40][O:41][CH2:42][C:43]([O:45]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:44])[C:15]([NH:17][CH:18]2[C:38](=[O:39])[N:20]3[C:21]([C:27]([O:29][CH2:30][O:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[O:28])=[C:22]([CH:25]=[CH2:26])[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1.C1(OC)C=CC=CC=1.C(OC(C)C)(C)C>C(Cl)Cl>[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:40][O:41][CH2:42][C:43]([OH:45])=[O:44])[C:15]([NH:17][CH:18]2[C:38](=[O:39])[N:20]3[C:21]([C:27]([O:29][CH2:30][O:31][C:32](=[O:37])[C:33]([CH3:34])([CH3:35])[CH3:36])=[O:28])=[C:22]([CH:25]=[CH2:26])[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 131713349HCID 131713349, compound

Product 1

HCID 131713348HCID 131713348, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5.75 g) was added to a solution of pivaloyloxymethyl 7-[2-(2-aminothiazol-4-yl)-2-benzhydryloxycarbonylmethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (3.7 g) in methylene chloride (14.8 ml) and anisole (1.09 g) under ice-cooling, and the mixture was stirred for an hour at ambient temperature. Then the reaction mixture was added dropwise to diisopropyl ether (160 ml). The precipitates were collected by filtration and washed with diisopropyl ether, followed by adding them to a mixture of water (60 ml) and ethyl acetate (60 ml). The resultant mixture was adjusted to pH 7.0 with a saturated aqueous sodium bicarbonate. The separated aqueous solution was further adjusted to pH 2.5 with 10% hydrochloric acid. The precipitates were collected by filtration, washed with water and then dried over phosphorus pentoxide in vacuo to give pivaloyloxymethyl 7-[2-(2-aminothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (2.13 g).

Workup

  1. temperaturecooling
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with diisopropyl ether
  4. additionby adding them
  5. additionto a mixture of water (60 ml) and ethyl acetate (60 ml)
  6. filtrationThe precipitates were collected by filtration
  7. washwashed with water
  8. dry with materialdried over phosphorus pentoxide in vacuo

Sources & evidence

ORD record
ord-68c508672d3546b2a2b257618106bba9
Source dataset
uspto-grants-1988_03
Patent number
US04731443

Reaction notes

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