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

HRID 1941581ノート

反応式

HRID 1941581 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7977ba4b6ce848ae9f3f86c35c1c7b20
出典データセット
uspto-grants-1997_12
特許番号
US05703243

反応ノート

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