Dicyclohexylcarbodiimide → (4-oxo-4-(2-oxo-1-pyrrolidinyl)butanoyl]-L-prolinol

HRID 892611Notes

Reaction equation

HRID 892611 reaction equation
[O:1]=[C:2]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13])[CH2:3][CH2:4][C:5]([OH:7])=O.[NH:14]1[CH2:20][CH2:19][CH2:18][C@H:15]1[CH2:16][OH:17].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[O:1]=[C:2]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13])[CH2:3][CH2:4][C:5]([N:14]1[CH2:20][CH2:19][CH2:18][C@H:15]1[CH2:16][OH:17])=[O:7]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 640091L-ProlinolHCID 148114614-Oxo-4-(2-oxo-1-pyrrolidinyl)butyric acid

Product 1

HCID 54104429(4-oxo-4-(2-oxo-1-pyrrolidinyl)butanoyl]-L-prolinol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-oxo-4-(2-oxo-1-pyrrolidinyl)butyric acid (5.02 g), L-prolinol (2.74 g) and HOBt (3.72 g) in DMF (50 ml) was cooled to -25° C. and DCC (5.64 g) was added thereto. After 3 hours' stirring at a temperature of -25°-0° C., the mixture was stirred at room temperature for 15 hours. The precipitated dicyclohexylurea was filtered off, and the filtrate was concentrated. The residue was dissolved in chloroform and washed with 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate and saturated brine in sequence. The organic layer was dried over magnesium sulfate, followed by concentration. The residue was purified by silica gel column chromatography (chloroform-methanol) to give 3.41 g of N-[(4-oxo-4-(2-oxo-1-pyrrolidinyl)butanoyl]-L-prolinol.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 hours
  2. filtrationThe precipitated dicyclohexylurea was filtered off
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with 1N hydrochloric acid
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationfollowed by concentration
  8. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-44345b8b5bd84a97891570ccac693305
Source dataset
uspto-grants-1992_06
Patent number
US05118811

Reaction notes

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