Hydrazine hydrate (1:1) → (2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-aminomethyl-4-mercaptopyrrolidine

HRID 1941581노트

반응식

HRID 1941581 반응식
[N+:1]([C:4]1[CH:34]=[CH:33][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17]C(=O)C)[CH2:14][C@H:13]2[CH2:21][N:22]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]([SH:17])[CH2:14][C@H:13]2[CH2:21][NH2:22])=[O:11])=[CH:33][CH:34]=1)([O-:3])=[O:2]

참가 물질

5

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 57106506(2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-acetylthiopyrrolidine

생성물 1

HCID 57083137(2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-aminomethyl-4-mercaptopyrrolidine수율 104.1%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-acetylthiopyrrolidine (4.92 g: 10.18 mmole) in a mixture of dichloromethane (15 ml) and methanol (75 ml), hydrazine hydrate (1.53 ml: 3 eq.) is added. The mixture is warmed to remove dichloromethane and heated to reflux for 1 hour and 10 minutes. The reaction mixture is concentrated in vacuo. The residue is diluted with dichloromethane and filtered. 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-mercaptopyrrolidine (3.3 g). Yield: Quantitative.

후처리

  1. additionis added
  2. temperatureThe mixture is warmed
  3. customto remove dichloromethane
  4. temperatureheated
  5. temperatureto reflux for 1 hour and 10 minutes
  6. concentrationThe reaction mixture is concentrated in vacuo
  7. additionThe residue is diluted with dichloromethane
  8. filtrationfiltered
  9. washThe filtrate is washed with water
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7977ba4b6ce848ae9f3f86c35c1c7b20
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05703243

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