Water → (2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-[5-(4-nitrobenzyloxycarbonylamino)-1,3-dioxan-2-yl]pyrrolidine

HRID 37269

반응식

HRID 37269 반응식
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][O:9][C:10]([NH:12][CH:13]([CH2:16][OH:17])[CH2:14][OH:15])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:20]([S:23][C@@H:24]1[CH2:28][N:27]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])[C@H:26]([CH:42]=O)[CH2:25]1)(=[O:22])[CH3:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:20]([S:23][C@@H:24]1[CH2:28][N:27]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])[C@H:26]([CH:42]2[O:17][CH2:16][CH:13]([NH:12][C:10]([O:9][CH2:8][C:7]3[CH:18]=[CH:19][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)=[O:11])[CH2:14][O:15]2)[CH2:25]1)(=[O:22])[CH3:21]

참가 물질

7

반응물 4

HCID 962Water2회HCID 6101p-Toluenesulfonic acidHCID 18638815(2S,4S)-4-acetylthio-2-formyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidineHCID 199345222-(4-Nitrobenzyloxycarbonyl)amino-1,3-propanediol

생성물 1

HCID 18638810(2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-[5-(4-nitrobenzyloxycarbonylamino)-1,3-dioxan-2-yl]pyrrolidine수율 85.7%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2-(4-nitrobenzyloxycarbonyl)amino-1,3-propanediol (1.42 g), (2S,4S)-4-acetylthio-2-formyl-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (1.00 g) and 4-toluene-sulfonic acid (0.30 g) in toluene was refluxed for 2 hours with removing water under azeotropic condition. The reaction mixture was poured into a mixture of water and ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (80 ml) and eluted with a mixture of acetone and dichloromethane (1:9, V/V) to give (2S, 4S)-4-acetylthio-1- (4-nitrobenzyloxycarbonyl)-2-[5-(4-nitrobenzyloxycarbonylamino) -1,3-dioxan-2-yl]pyrrolidine (1.47 g).

후처리

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel (80 ml)
  6. washeluted with a mixture of acetone and dichloromethane (1:9, V/V)

출처 및 근거

ORD 기록
ord-ae36b222e23a4aec9fa43903c97c4233
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420122

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