Citric Acid → 5-Oxazolidinepropanoic acid, 3-[(1,1-dimethylethoxy)carbonyl]-4-[(2S)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutyl]-2,2-dimethyl-alpha-(1-methylethyl)-, (alphaS,4S,5S)-

HRID 744832노트

반응식

HRID 744832 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C@@H:14]([CH:30]([CH3:32])[CH3:31])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:11]([CH2:33][C@H:34]([CH:38]=[O:39])[CH:35]([CH3:37])[CH3:36])[O:10][C:9]1([CH3:41])[CH3:40])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Mn]([O-])(=O)(=O)=[O:43].[K+].S([O-])([O-])=O.[Na+].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C@@H:14]([CH:30]([CH3:32])[CH3:31])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:11]([CH2:33][C@H:34]([C:38]([OH:43])=[O:39])[CH:35]([CH3:36])[CH3:37])[O:10][C:9]1([CH3:40])[CH3:41])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 311Citric AcidHCID 24437Sodium SulfiteHCID 516875Potassium PermanganateHCID 236253323-Tert-butoxycarbonyl-5(S)-(2(S)-formyl-3-methyl-butyl)-4(S)-(2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)phenyl]-propyl}-2,2-dimethyl-1,3-oxazolidine

생성물 1

HCID 236254795-Oxazolidinepropanoic acid, 3-[(1,1-dimethylethoxy)carbonyl]-4-[(2S)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutyl]-2,2-dimethyl-alpha-(1-methylethyl)-, (alphaS,4S,5S)-

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매2회HCID 1140Toluene용매

실험 절차

53 g of 3-tert-butoxycarbonyl-5(S)-(2(S)-formyl-3-methyl-butyl)-4(S)-{2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-propyl}-2,2-dimethyl-1,3-oxazolidine are dissolved in 470 ml of toluene, and, at 0° C., 470 ml of water, 79.1 g of potassium permanganate and 9.7 g of tetrabutylammonium bromide are added in succession thereto. The reaction mixture is stirred for a further 48 hours at 0°-5° C., and then, at 10° C., 1.2 liters of 10% sodium sulfite solution are added. After a further 30 minutes, 1.95 liters of 10% citric acid solution and 1.2 liters of water are added. The product is extracted by repeated extraction with ethyl acetate. The extracts are concentrated by evaporation and purified by FC (2.3 kg of silica gel, ethyl acetate/hexane=3:7). The title compound is obtained: Rf (ethyl acetate/hexane=1:2)=0.21.

후처리

  1. waitAfter a further 30 minutes
  2. extractionThe product is extracted
  3. extractionextraction with ethyl acetate
  4. concentrationThe extracts are concentrated by evaporation
  5. custompurified by FC (2.3 kg of silica gel, ethyl acetate/hexane=3:7)

출처 및 근거

ORD 기록
ord-daeb8ec8d5294c11926522ca905733a0
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05559111

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