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 744833ノート

反応式

HRID 744833 の反応式
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]

参加物

5

反応物 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)-

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-694b728ec3a54755889cfbd56cdc332f
出典データセット
uspto-grants-1996_09
特許番号
US05559111

反応ノート

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