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

HRID 892616Notes

Reaction equation

HRID 892616 reaction equation
[O:1]=[C:2]([NH:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][C:19]1=[O:23])[CH2:3][CH2:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][C@H:8]1[CH2:9][OH:10])=[O:6]>C1C=CC=CC=1.CS(C)=O.C(N(CC)CC)C>[O:1]=[C:2]([NH:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][C:19]1=[O:23])[CH2:3][CH2:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][C@H:8]1[CH:9]=[O:10])=[O:6]

Participants

5

Reactant 1

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

Product 1

HCID 54280415N-{4-oxo-4-[3-(2-oxo-1-pyrrolidinyl)propylamino]butanoyl}-L-prolinalYield 65.1%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 679Dimethyl SulfoxideSolventHCID 8471TriethylamineSolvent

Procedure

N-{4-Oxo-4-[3-(2-oxo-1-pyrrolidinyl)propylamino]butanoyl}-L-prolinol (85 mg) was dissolved in a mixed solvent of benzene (0.18 ml), DMSO (0.5 ml) and triethylamine (0.18 ml), and sulfur trioxide pyridine complex (200 mg) was added thereto under ice-cooling. After 1 hour's stirring at a temperature of 10°-15° C., the reaction mixture was treated in the same manner as in Example 10-C) to give 55 mg of N-{4-oxo-4-[3-(2-oxo-1-pyrrolidinyl)propylamino]butanoyl}-L-prolinal.

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. additionthe reaction mixture was treated in the same manner as in Example 10-C)

Sources & evidence

ORD record
ord-6dd016ef147d4ebaa6e1a4b03a042aee
Source dataset
uspto-grants-1992_06
Patent number
US05118811

Reaction notes

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