4-Phenylbutyric Acid → HCID 54035213, compound

HRID 1720474Notes

Reaction equation

HRID 1720474 reaction equation
CN1CCOCC1.[C:8]1([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[CH2:21]([O:28][C:29](=[O:35])[C@@H:30]1[CH2:34][CH2:33][CH2:32][NH:31]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[CH2:21]([O:28][C:29](=[O:35])[C@@H:30]1[CH2:34][CH2:33][CH2:32][N:31]1[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 47754-Phenylbutyric AcidHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 2733413Proline benzyl ester hydrochloride

Product 1

HCID 54035213HCID 54035213, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-25 °C

Procedure

N-Methylmorpholine (3.4 ml) and 4-phenylbutyric acid (5.02 g) were added to L-proline benzyl ester hydrochloride (7.37 g) in dichloromethane (80 ml) under ice-cooling. The mixture was cooled to -25° C., added with DCC (6.31 g) and stirred at room temperature for 16 hours. The resultant dicyclohexylurea was filtered off and the filtrate was concentrated. The residue was purified by silica gel column chromatography (eluate: chloroform-methanol) to give 9.42 g of N-(4-phenylbutyryl)-L-proline benzyl ester.

Workup

  1. temperaturecooling
  2. filtrationThe resultant dicyclohexylurea was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatography (eluate: chloroform-methanol)

Sources & evidence

ORD record
ord-7712e706351d4f76b8d2ccafb8ed6c35
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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