Hydrazine hydrate (1:1) → (2S,4S)-2-aminomethyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine

HRID 1941574노트

반응식

HRID 1941574 반응식
[N+:1]([C:4]1[CH:50]=[CH:49][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH2:37][N:38]2C(=O)C3=CC=CC=C3C2=O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].O.NN>ClCCl.CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:14][C@H:13]2[CH2:37][NH2:38])=[O:11])=[CH:49][CH:50]=1)([O-:3])=[O:2]

참가 물질

5

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 57302820(2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-tritylthiopyrrolidine

생성물 1

HCID 15056148(2S,4S)-2-aminomethyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine수율 91%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-tritylthiopyrrolidine (10.46 g: 15.31 mmole) in a mixture of dichloromethane (80 ml) and methanol (160 ml), hydrazine hydrate (1.53 ml: 2 eq.) is added, and the mixture is concentrated to remove dichloromethane by warming and refluxed for 3 hours and 15 minutes. The reaction mixture is concentrated in vacuo. The residue is diluted with dichloromethane and filtered to remove solid. The filtrate is washed with water, dried over magnesium sulfate, and concentrated in vacuo to give crude (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-aminomethyl-4-tritylthiopyrrolidine (7.71 g). Yield: 91%.

후처리

  1. additionis added
  2. concentrationthe mixture is concentrated
  3. customto remove dichloromethane
  4. temperatureby warming
  5. temperaturerefluxed for 3 hours and 15 minutes
  6. concentrationThe reaction mixture is concentrated in vacuo
  7. additionThe residue is diluted with dichloromethane
  8. filtrationfiltered
  9. customto remove solid
  10. washThe filtrate is washed with water
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-496d948219ad4547a6400f2a22f3dd7a
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05703243

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