N2 (benzyloxycarbonyl)-4(R)-(tert-butoxyformamido)-N1-tert.butyl-L-prolinamide → 4(R)-(tert-butoxyformamido)-N1-tert.butyl-L-prolinamide

HRID 1757766Notes

Reaction equation

HRID 1757766 reaction equation
N#N.C(OC([C@@:13]1([C:30]([NH2:32])=[O:31])[CH2:17][C@@H:16]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][N:14]1[C:26]([CH3:29])([CH3:28])[CH3:27])=O)C1C=CC=CC=1>C(O)C.[Pd]>[C:22]([O:21][C:19]([NH:18][C@H:16]1[CH2:15][N:14]([C:26]([CH3:29])([CH3:28])[CH3:27])[C@H:13]([C:30]([NH2:32])=[O:31])[CH2:17]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 1

HCID 86746286N2 (benzyloxycarbonyl)-4(R)-(tert-butoxyformamido)-N1-tert.butyl-L-prolinamide

Product 1

HCID 572672704(R)-(tert-butoxyformamido)-N1-tert.butyl-L-prolinamideYield 106.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.25 g of N2 -(benzyloxycarbonyl)-4(R)-(tert-butoxyformamido)-N1 -tert.butyl-L-prolinamide was dissolved in ethanol and hydrogenated over 0.1 g of 10% palladium-on-carbon at room temperature and under atmosphericpressure for 4 hours. The catalyst was filtered off and the filtrate was evaporated to give 0.17 g of 4(R)(tert.butoxyformamido)-N1 -tert.butyl-L-prolinamide as a glass which was used without further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-9f63b3947972468a93fcb5f70eb98c05
Source dataset
uspto-grants-1995_08
Patent number
US05446161

Reaction notes

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