HCID 15598570, compound → HCID 22691414, compound

HRID 476989Notes

Reaction equation

HRID 476989 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:28])[C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1C(OCC1C=CC=CC=1)=O)=[O:4]>C(O)C.[Pd].[C]>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:28])[C@@H:13]1[CH2:17][CH2:16][CH2:15][NH:14]1)=[O:4]

Participants

4

Reactant 1

HCID 15598570HCID 15598570, compound

Product 1

HCID 22691414HCID 22691414, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 20 ml of ethanol was dissolved 1.9 g of N-benzyloxycarbonyl-(S)-proline 2-methoxycarbonylphenylamide prepared in Reference Example 39. To the solution was added 1 g of 10% Pd-carbon and the mixture was hydrogenated at ambient temperature and under atomspheric pressure. After 1.5 hours, the catalyst was removed by filtration and the filtrate was distilled off under reduced pressure. To the residue was added ether. The precipitated crystals were collected by filtration, giving 950 mg of (S)-proline 2-methoxycarbonylphenylamide.

Workup

  1. customprepared in Reference Example 39
  2. customwas hydrogenated at ambient temperature and under atomspheric pressure
  3. customthe catalyst was removed by filtration
  4. distillationthe filtrate was distilled off under reduced pressure
  5. additionTo the residue was added ether
  6. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-d50a81e76a1b4c16bdfd453cb8a3aaab
Source dataset
uspto-grants-1989_12
Patent number
US04886813

Reaction notes

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