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

HRID 704410Notes

Reaction equation

HRID 704410 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([NH:26][C@H:27]([C:30]([OH:32])=O)[CH2:28][OH:29])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].[C:33]1([CH2:39][CH2:40][CH2:41][N:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.OS1C2C=CC=CC=2N=C1>CN(C)C=O.C(OCC)(=O)C>[CH2:19]([O:18][C:16]([NH:26][CH:27]([CH2:28][OH:29])[C:30]([N:45]1[CH2:46][CH2:47][N:42]([CH2:41][CH2:40][CH2:39][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:43][CH2:44]1)=[O:32])=[O:17])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 100310N-(Benzyloxycarbonyl)-L-serineHCID 7965341-(3-Phenylpropyl)piperazineHCID 178527226HCID 178527226, compound

Product 1

HCID 148815491-[2-(Benzyloxycarbonylamino)-3-hydroxypropionyl]-4-(3-phenylpropyl)piperazineYield 73.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dicyclohexylcarbodiimide (1.58 g) was added to an ice-cooled solution of 2.0 g of N-carbobenzyloxyserine, 1.57 g of 1-(3-phenylpropyl)piperazine and 1.04 g of 1-hydroxybenzotiazole in 30 ml of N,N-dimethylformamide. The mixture was stirred at room temperature for 24 hours, then diluted with ethyl acetate, washed in sequence with two portions of 4% aqueous sodium hydrogen carbonate, one portion of water and one portion of saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 2.39 g of 1-[2-(benzyloxycarbonylamino)-3-hydroxypropionyl]-4-(3-phenylpropyl}piperazine. Melting point 95°-97° C.

Workup

  1. washwashed in sequence with two portions of 4% aqueous sodium hydrogen carbonate, one portion of water and one portion of saturated aqueous solution of sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3046f51986a644cea6a3ac80c2e3dd47
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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