4-((S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonyl-propionyl)-piperazine-1-carboxylic acid ethyl ester → 4-((S)-2-amino-3-tert-butoxycarbonyl-propionyl)-piperazine-1-carboxylic acid ethyl ester

HRID 553810Notes

Reaction equation

HRID 553810 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:33])[C@@H:13]([NH:22]C(OCC2C=CC=CC=2)=O)[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:8][CH2:7]1)=[O:5])[CH3:2]>CC(=O)OCC.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12](=[O:33])[C@@H:13]([NH2:22])[CH2:14][C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 669202694-((S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonyl-propionyl)-piperazine-1-carboxylic acid ethyl ester

Product 1

HCID 668549254-((S)-2-amino-3-tert-butoxycarbonyl-propionyl)-piperazine-1-carboxylic acid ethyl esterYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-((S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonyl-propionyl)-piperazine-1-carboxylic acid ethyl ester (3.27 g) was hydrogenated in EA (25 ml) with Pd/C (10%, 327 mg) overnight. The mixture was filtered through celite and evaporated off. HV drying afforded 2.29 g of the desired compound.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated off
  3. customHV drying

Sources & evidence

ORD record
ord-dcefc09f110f4575a0e651bbc83ec2ac
Source dataset
uspto-grants-2011_11
Patent number
US08048881B2

Reaction notes

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