1-[2-(Benzyloxycarbonylamino)-3-hydroxypropionyl]-4-(3-phenylpropyl)piperazine → 1-(2-Amino-3-hydroxypropionyl)-4-(3-phenylpropyl)piperazine

HRID 704411Notes

Reaction equation

HRID 704411 reaction equation
C(OC([NH:11][CH:12]([CH2:30][OH:31])[C:13]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:17][CH2:16]1)=[O:14])=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][CH:12]([CH2:30][OH:31])[C:13]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:17][CH2:16]1)=[O:14]

Participants

4

Reactant 1

HCID 148815491-[2-(Benzyloxycarbonylamino)-3-hydroxypropionyl]-4-(3-phenylpropyl)piperazine

Product 1

HCID 200740861-(2-Amino-3-hydroxypropionyl)-4-(3-phenylpropyl)piperazineYield 104.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium-on-carbon (100 mg) was added to a solution of 1.12 g of 1-[2-(benzyloxycarbonylamino)-3-hydroxypropionyl]-4-(3-phenylpropyl)piperazine in 30 ml of ethanol, and the mixture was stirred under a hydrogen gas stream until cessation of hydrogen absorption. The catalyst was then filtered off, and the filtrate was concentrated under reduced pressure to give 800 mg of 1-(2-amino-3-hydroxypropionyl)-4-(3-phenylpropyl)piperazine.

Workup

  1. customuntil cessation of hydrogen absorption
  2. filtrationThe catalyst was then filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8f5132a552d44df0b951bd761d9a6eb4
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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