Hydrazine hydrate (1:1) → HCID 57228294, compound

HRID 1941588Notes

Reaction equation

HRID 1941588 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([S:13]C(=O)C)[CH2:10][C@H:9]1[CH2:17][N:18]1C(=O)C2=CC=CC=C2C1=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN>ClCCl.CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([SH:13])[CH2:10][C@H:9]1[CH2:17][NH2:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57126089HCID 57126089, compound

Product 1

HCID 57228294HCID 57228294, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-1-t-butoxycarbonyl-2-phthalimidomethyl-4-acetylthiopyrrolidine (8.58 g) in a mixture of dichloromethane (26 ml) and methanol (129 ml), hydrazine hydrate (4.11 ml) is added. The mixture is heated to reflux for 2 hours and 45 minutes and filtered. The filtrate is concentrated in vacuo. The residue is dissolved in dichloromethane, washed with water, dried over sodium sulfate, and concentrated in vacuo to give crude (2S,4S)-1-t-butoxycarbonyl-2-aminomethyl-4-mercaptopyrrolidine (4.1 g). Yellow syrup.

Workup

  1. additionis added
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 2 hours and 45 minutes
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated in vacuo
  6. dissolutionThe residue is dissolved in dichloromethane
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce9d857e0c874f8f93f9f2470b0843fb
Source dataset
uspto-grants-1997_12
Patent number
US05703243

Reaction notes

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