Tetrapropylammonium → 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

HRID 2256746노트

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HRID 2256746 반응식
C[N+]1([O-])CCOCC1.[C:9]([O:13][C:14]([N:16]1[C@@H:20]([CH2:21][C@@H:22]([CH:38]([CH3:40])[CH3:39])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH2:33][CH2:34][CH2:35][O:36][CH3:37])[CH:25]=2)[C@H:19]([CH2:41][C@@H:42]([CH:45]([CH3:47])[CH3:46])[CH2:43][OH:44])[O:18][C:17]1([CH3:49])[CH3:48])=[O:15])([CH3:12])([CH3:11])[CH3:10].C([N+](CCC)(CCC)CCC)CC>ClCCl>[C:9]([O:13][C:14]([N:16]1[C@@H:20]([CH2:21][C@@H:22]([CH:38]([CH3:40])[CH3:39])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH2:33][CH2:34][CH2:35][O:36][CH3:37])[CH:25]=2)[C@H:19]([CH2:41][C@H:42]([CH:43]=[O:44])[CH:45]([CH3:46])[CH3:47])[O:18][C:17]1([CH3:48])[CH3:49])=[O:15])([CH3:12])([CH3:11])[CH3:10]

참가 물질

5

반응물 3

HCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 236253313-Oxazolidinecarboxylic acid, 5-[(2S)-2-(hydroxymethyl)-3-methylbutyl]-4-[(2S)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4S,5S)-

생성물 1

HCID 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

100 g of molecular sieve (0.3 nm) and 16.6 g of N-methylmorpholine-N-oxide are added to 53 g of 3-tert-butoxycarbonyl-5(S)-(3-hydroxy-2(S)-isopropyl-propyl)-4(S)-{2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-propyl}-2,2-dimethyl-1,3-oxazolidine in 1.8 liters of dichloromethane at room temperature. The reaction mixture is stirred for 10 minutes and then 1.60 g of tetrapropylammonium perrutherate are added. The reaction mixture is stirred for a further 30 minutes and then filtered. The filtrate is diluted with dichloromethane and then washed in succession with 2M sodium sulfite solution, saturated sodium chloride solution and 1M copper(II) sulfate. The organic phase is concentrated by evaporation and the crude title compound is obtained: Rf (ethyl acetate/hexane=1:2)=0.43.

후처리

  1. stirringThe reaction mixture is stirred for a further 30 minutes
  2. filtrationfiltered
  3. additionThe filtrate is diluted with dichloromethane
  4. washwashed in succession with 2M sodium sulfite solution, saturated sodium chloride solution and 1M copper(II) sulfate
  5. concentrationThe organic phase is concentrated by evaporation

출처 및 근거

ORD 기록
ord-485ad111870a48e19576ea04bb722afd
출처 데이터셋
uspto-grants-1997_08
특허 번호
US05654445

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