Acetic Acid → 3-(4-(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-hydroxymethyloxazolidin-2-one

HRID 8176노트

반응식

HRID 8176 반응식
[CH3:1][C:2]1([CH3:34])[O:6][C@H:5]([C:7]([N:9]2[CH2:14][CH2:13][C:12]([C:15]3[C:20]([F:21])=[CH:19][C:18]([N:22]4[CH2:26][C@H:25]([CH2:27][O:28]C(=O)C)[O:24][C:23]4=[O:32])=[CH:17][C:16]=3[F:33])=[CH:11][CH2:10]2)=[O:8])[CH2:4][O:3]1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>CO>[CH3:1][C:2]1([CH3:34])[O:6][C@H:5]([C:7]([N:9]2[CH2:14][CH2:13][C:12]([C:15]3[C:16]([F:33])=[CH:17][C:18]([N:22]4[CH2:26][C@H:25]([CH2:27][OH:28])[O:24][C:23]4=[O:32])=[CH:19][C:20]=3[F:21])=[CH:11][CH2:10]2)=[O:8])[CH2:4][O:3]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 207256423-(4(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one

생성물 1

HCID 207256433-(4-(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-hydroxymethyloxazolidin-2-one수율 92.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

3-(4-(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one (8.64 g, 18 mM) was suspended in methanol (350 ml) and stirred at ambient temperature under nitrogen. Potassium carbonate (3.73 g, 27 mM) was added, and the mixture stirred for 20 minutes only, then neutralised immediately by the addition of acetic acid (2 ml). Saturated aqueous sodium bicarbonate (50 ml) was added, the methanol evaporated, and the residue diluted with water (100 ml) before extraction of the organics into dichloromethane (250 ml+100 ml). The extract was washed with brine (100 ml), dried (magnesium sulfate), evaporated and crude product purified by chromatography on a 300 g silica vacuum sinter column, eluting with a gradient from 0% to 20% methanol in dichloromethane. Relevant fractions were combined to give the desired product (7.3 g).

후처리

  1. stirringthe mixture stirred for 20 minutes only
  2. customthe methanol evaporated
  3. additionthe residue diluted with water (100 ml) before extraction of the organics into dichloromethane (250 ml+100 ml)
  4. washThe extract was washed with brine (100 ml)
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. customcrude product purified by chromatography on a 300 g silica vacuum sinter column
  8. washeluting with a gradient from 0% to 20% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-b1d02d975dd644069dccecc38e8a3752
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087629B2

반응 노트

불러오는 중…