Dicyclohexylcarbodiimide → N-{4-oxo-4-[3-(2-oxo-1-pyrrolidinyl)propylamino]butanoyl}-L-prolinol

HRID 892615Notes

Reaction equation

HRID 892615 reaction equation
[O:1]=[C:2]([NH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][C:13]1=[O:17])[CH2:3][CH2:4][C:5]([OH:7])=O.[NH:18]1[CH2:24][CH2:23][CH2:22][C@H:19]1[CH2:20][OH:21].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[O:1]=[C:2]([NH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][C:13]1=[O:17])[CH2:3][CH2:4][C:5]([N:18]1[CH2:24][CH2:23][CH2:22][C@H:19]1[CH2:20][OH:21])=[O:7]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 640091L-ProlinolHCID 198959194-Oxo-4-[3-(2-oxo-1-pyrrolidinyl)propylamino]butyric acid

Product 1

HCID 54573583N-{4-oxo-4-[3-(2-oxo-1-pyrrolidinyl)propylamino]butanoyl}-L-prolinolYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-oxo-4-[3-(2-oxo-1-pyrrolidinyl)propylamino]butyric acid (255 mg) and L-prolinol (118 mg) in DMF (5 ml) were added HOBt (157 mg) and DCC (249 mg) at -25° C. and the mixture was stirred at a temperature of -25°-0° C. for 3 hours. After 15 hours' stirring at room temperature, the precipitated dicyclohexylurea was filtered off, and the filtrate was concentrated. The residue was treated in the same manner as in Example 10-B) to give 189 mg of N-{4-oxo-4-[3-(2-oxo-1-pyrrolidinyl)propylamino]butanoyl}-L-prolinol.

Workup

  1. stirringAfter 15 hours' stirring at room temperature
  2. filtrationthe precipitated dicyclohexylurea was filtered off
  3. concentrationthe filtrate was concentrated
  4. additionThe residue was treated in the same manner as in Example 10-B)

Sources & evidence

ORD record
ord-48bd4a3e027d4ae195377684f33ec795
Source dataset
uspto-grants-1992_06
Patent number
US05118811

Reaction notes

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