Trifluoroacetic acid → HCID 131714999, compound

HRID 1249422Notes

Reaction equation

HRID 1249422 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:46][O:47][CH3:48])[C:15]([NH:17][CH:18]2[C:44](=[O:45])[N:20]3[C:21]([C:28]([O:30]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:29])=[C:22](/[CH:25]=[CH:26]/[Cl:27])[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1.C(OC(C)C)(C)C>C(Cl)Cl.C1(OC)C=CC=CC=1>[CH3:48][O:47][N:46]=[C:14]([C:12]1[N:13]=[C:9]([NH2:8])[S:10][CH:11]=1)[C:15]([NH:17][CH:18]1[C:44](=[O:45])[N:20]2[C:21]([C:28]([OH:30])=[O:29])=[C:22](/[CH:25]=[CH:26]/[Cl:27])[CH2:23][S:24][C@H:19]12)=[O:16]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131715000HCID 131715000, compound

Product 1

HCID 131714999HCID 131714999, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (6 ml) was added to a solution of benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylate (syn isomer) (1.4 g) in methylene chloride (4 ml) and anisole (1.4 ml) under ice-cooling and the mixture was stirred at the same temperature for 40 minutes. The resulting solution was added dropwise to diisopropyl ether (200 ml) and the resultant precipitates were collected by filtration. The precipitates were added to a mixture of water (30 ml) and ethyl acetate (30 ml) and the solution was adjusted to pH 7.0 with 5% aqueous solution of sodium bicarbonate. The separated aqueous layer was adjusted to pH 2.7 with 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylic acid (syn isomer) (0.66 g).

Workup

  1. temperaturecooling
  2. customthe resultant precipitates
  3. filtrationwere collected by filtration
  4. additionThe precipitates were added to a mixture of water (30 ml) and ethyl acetate (30 ml)
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3b805e02992645c790d31fb92fc7528a
Source dataset
uspto-grants-1986_12
Patent number
US04631274

Reaction notes

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