N2 [3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-(2-naphthyl)butyl]-N1-tert.butyl-L-prolinamide → N2 [3(S)-amino-2(R)-hydroxy-L-(2-naphthyl)butyl]-N1-tert.butyl-L-prolinamide

HRID 267153Notes

Reaction equation

HRID 267153 reaction equation
[N:1]#[N:2].C(OC([NH:13][C@@H:14]([CH2:30][C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=1)[C@H:15]([OH:29])[CH2:16][C@@:17]1([C:26]([NH2:28])=[O:27])[CH2:21][CH2:20][CH2:19][N:18]1[C:22]([CH3:25])([CH3:24])[CH3:23])=O)C1C=CC=CC=1>C(O)C.[Pd]>[N:1]#[N:2].[NH2:13][C@@H:14]([CH2:30][C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=1)[C@H:15]([OH:29])[CH2:16][C@@:17]1([C:26]([NH2:28])=[O:27])[CH2:21][CH2:20][CH2:19][N:18]1[C:22]([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 1

HCID 86746265N2 [3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-(2-naphthyl)butyl]-N1-tert.butyl-L-prolinamide

Product 1

HCID 86746264N2 [3(S)-amino-2(R)-hydroxy-L-(2-naphthyl)butyl]-N1-tert.butyl-L-prolinamideYield 98.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.725 g of N2 -[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-(2-naphthyl)butyl]-N1 -tert.butyl-L-prolinamide was dissolved in 25 ml of ethanol and hydrogenated at room temperature and under atmospheric pressure over 0.5 g of 10% palladium-on-carbon for 20 hours. The catalyst was filtered off and the filtrate was evaporated to give 0.54 g of N2 -[3(S)-amino-2(R)-hydroxy-L-(2-naphthyl)butyl]-N1 -tert.butyl-L-prolinamide as a white foam which was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-c218a31d73d74f4f8ebc991cd2b74d0a
Source dataset
uspto-grants-1997_07
Patent number
US05652369

Reaction notes

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