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

HRID 1154177노트

반응식

HRID 1154177 반응식
C(=[N:8][CH:9]1[C:34](=[O:35])[N:11]2[C:12]([C:18]([O:20]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:19])=[C:13]([CH:16]=[CH2:17])[CH2:14][S:15][C@H:10]12)C1C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C1(OC)C=CC=CC=1.C(OCC)(=O)C>[NH2:8][CH:9]1[C:34](=[O:35])[N:11]2[C:12]([C:18]([OH:20])=[O:19])=[C:13]([CH:16]=[CH2:17])[CH2:14][S:15][C@H:10]12

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 12818010Benzhydryl 7-benzylideneamino-3-vinyl-3-cephem-4-carboxylate

생성물 1

HCID 128180067-Amino-3vinyl-3-cephem-4-carboxylic acid수율 49.4%

시약·촉매·용매 2

HCID 7519Anisole용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of benzhydryl 7-benzylideneamino-3-vinyl-3-cephem-4-carboxylate (8.6 g) in anisole (10 ml) was added dropwise trifluoroacetic acid (10 ml) at -20° C., and the reaction temperature was gradually raised to ambient temperature with stirring, followed by stirring at ambient temperature for half an hour. The reaction mixture was poured into a mixture of ethyl acetate (100 ml) and a saturated aqueous sodium bicarbonate (100 ml), and then the mixture was adjusted to pH 7.5 with 20% aqueous sodium carbonate. The separated aqueous solution was washed with ethyl acetate (100 ml) and adjusted to pH 7.2 with conc. hydrochloric acid, followed by subjecting to column chromatography on alumina (10 ml). Elution was carried out with 15% aqueous sodium chloride, and fractions containing a desired compound were collected and then adjusted to pH 3.3 with conc. hydrochloric acid. The precipitated crystals were collected by filtration, washed with acetone and dried to obtain 7-amino-3-vinyl-3-cephem-4-carboxylic acid (2.0 g), mp 200°-230° C. (dec.).

후처리

  1. stirringby stirring at ambient temperature for half an hour
  2. washThe separated aqueous solution was washed with ethyl acetate (100 ml)
  3. washElution
  4. additioncontaining a desired compound
  5. customwere collected
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with acetone
  8. customdried

출처 및 근거

ORD 기록
ord-f9f5f2d0de0843ab81ad4bb94a93bdfb
출처 데이터셋
uspto-grants-1984_12
특허 번호
US04487927

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