Methanol → tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-(1,2,3-trihydroxypropan-2-yl)-1,4-oxazepane-4-carboxylate

HRID 1022809노트

반응식

HRID 1022809 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:15]([C:16]([OH:21])([CH:19]=C)[CH:17]=C)[O:14][CH2:13][CH2:12][N:11]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].O=[O+][O-].[BH4-].[Na+].[OH2:34].C[OH:36]>>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:15]([C:16]([OH:21])([CH2:17][OH:36])[CH2:19][OH:34])[O:14][CH2:13][CH2:12][N:11]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

6

반응물 5

HCID 887MethanolHCID 962WaterHCID 24823OzoneHCID 4311764Sodium borohydrideHCID 66976741tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-(3-hydroxypent-1,4-dien-3-yl)-1,4-oxazepane-4-carboxylate

생성물 1

HCID 66976366tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-(1,2,3-trihydroxypropan-2-yl)-1,4-oxazepane-4-carboxylate

실험 절차

Into a solution of tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-(3-hydroxypent-1,4-dien-3-yl)-1,4-oxazepane-4-carboxylate (2.31 g) in methanol (50 ml) was introduced an ozone gas (from ozone developing apparatus) at −78° C. with stirring. When the solution turned pale-blue, introduction was stopped, and a nitrogen gas was introduced instead until the pale-blue color disappeared. Sodium tetrahydroborate (612 mg) was added at −78° C., and the mixture was warmed with stirring to room temperature, and stirred for 10 min. Water was added to quench the reaction, methanol was evaporated under reduced pressure, and the residue was extracted three times with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (10%-100%)) to give the title compound (800 mg) as a colorless oil.

후처리

  1. additiona nitrogen gas was introduced instead until the pale-blue color
  2. temperaturethe mixture was warmed
  3. stirringwith stirring to room temperature
  4. stirringstirred for 10 min
  5. customto quench
  6. customthe reaction, methanol
  7. customwas evaporated under reduced pressure
  8. extractionthe residue was extracted three times with ethyl acetate
  9. washThe organic layer was washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. customthe solvent was evaporated
  12. customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (10%-100%))

출처 및 근거

ORD 기록
ord-fe43a4ed45c049f99a612c912ba94e08
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722662B2

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