Hydrazine hydrate (1:1) → HCID 10578323, compound

HRID 1034474Notes

Reaction equation

HRID 1034474 reaction equation
[CH3:1][O:2][C:3]1[CH:49]=[CH:48][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:15][C@@H:14]([S:16][C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][C@H:12]2[CH2:36][N:37]2C(=O)C3=CC=CC=C3C2=O)=[O:10])=[CH:5][CH:4]=1.O.NN>ClCCl.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:15][C@@H:14]([S:16][C:17]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][C@H:12]2[CH2:36][NH2:37])=[O:10])=[CH:48][CH:49]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10580299HCID 10580299, compound

Product 1

HCID 10578323HCID 10578323, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-1-p-methoxybenzyloxycarbonyl-2-phthalimidomethyl-4-tritylthiopyrrolidine (752 mg: 1.124 mmole) in a mixture of dichloromethane (3 ml) and methanol (12 ml), hydrazine hydrate (109 μl: 2 eq.) is added. The mixture is heated for 5 hours. The reaction mixture is concentrated in vacuo. The residue is dissolved in dichloromethane (5 ml) and the solid is filtered off. The filtrate is washed with water and concentrated in vacuo. The residue is recrystallized from a mixture of dichloromethane and methanol to give (2S,4S)-1-p-methoxybenzyloxycarbonyl-2-aminomethyl-4-tritylthiopyrrolidine (471 mg). Yield: 78%. mp. 165° to 167° C. NMR δ(CDCl3 :CD3OD=2:1) ppm: 3.46(s, 3H), 4.96, 4.89(ABq, J=12 Hz, 2H). IR ν (CHCl3) cm-1 : 1683, 1610.

Workup

  1. additionis added
  2. temperatureThe mixture is heated for 5 hours
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. dissolutionThe residue is dissolved in dichloromethane (5 ml)
  5. filtrationthe solid is filtered off
  6. washThe filtrate is washed with water
  7. concentrationconcentrated in vacuo
  8. customThe residue is recrystallized from a mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-980f4307a506496a8eebdb7558a7876c
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

Loading…