Hydrazine hydrate (1:1) → N-(4-aminobenzyl)-3-(t-butoxycarbonyl)thiazolidine-2-carboxamide

HRID 1250081Notes

Reaction equation

HRID 1250081 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][NH:9][C:10]([CH:12]2[N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:14][S:13]2)=[O:11])=[CH:6][CH:5]=1)([O-])=O.O.NN>CO.[Ni]>[NH2:1][C:4]1[CH:25]=[CH:24][C:7]([CH2:8][NH:9][C:10]([CH:12]2[N:16]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:15][CH2:14][S:13]2)=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21918695N-(4-nitrobenzyl)-3-(t-butoxycarbonyl)thiazolidine-2-carboxamide

Product 1

HCID 21918614N-(4-aminobenzyl)-3-(t-butoxycarbonyl)thiazolidine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A spatula tip's worth of Nickel of Raney is added to a solution of 1.25 g (3.4 mmoles) of N-(4-nitrobenzyl)-3-(t-butoxycarbonyl)thiazolidine-2-carboxamide in 2.5 ml of methanol. The whole is taken to reflux and hydrazine hydrate (1.75 ml) is added dropwise to the medium. The reaction is maintained for 1 hour under reflux, then returned to ambient temperature. The catalyst is filtered off and abundantly rinsed with methanol. The solvent is evaporated off under reduced pressure. Then the residue is taken up in dichloromethane (20 ml) and washed 3 times with 15 ml of water. The organic phase is dried and the solvent is evaporated off under reduced pressure. N-(4-aminobenzyl)-3-(t-butoxycarbonyl)thiazolidine-2-carboxamide is obtained in the form of an inert yellow solid (0.815 g, 71%); it will be used in following stages without further purification.

Workup

  1. temperatureto reflux
  2. temperatureThe reaction is maintained for 1 hour
  3. temperatureunder reflux
  4. customreturned to ambient temperature
  5. filtrationThe catalyst is filtered off
  6. washabundantly rinsed with methanol
  7. customThe solvent is evaporated off under reduced pressure
  8. washwashed 3 times with 15 ml of water
  9. customThe organic phase is dried
  10. customthe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record
ord-345555ed29854519906cdbd500d161c6
Source dataset
uspto-grants-2002_01
Patent number
US06335445B1

Reaction notes

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