Triethylamine → HCID 54542799, compound

HRID 892608Notes

Reaction equation

HRID 892608 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([N:10]1[CH2:23][CH2:22][CH2:21][C@H:11]1[C:12]([N:14]1[CH2:20][CH2:19][CH2:18][C@H:15]1[CH2:16][OH:17])=[O:13])=[O:9].C(N(CC)CC)C>CS(C)=O>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([N:10]1[CH2:23][CH2:22][CH2:21][C@H:11]1[C:12]([N:14]1[CH2:20][CH2:19][CH2:18][C@H:15]1[CH:16]=[O:17])=[O:13])=[O:9]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 53921892HCID 53921892, compound

Product 1

HCID 54542799HCID 54542799, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of N-[(2-oxo-1-pyrrolidinyl)acetyl]-L-prolyl-L-prolinol (965 mg) in DMSO (5 ml) were added triethylamine (2.5 ml) and sulfur trioxide pyridine complex (1.89 g) under ice-cooling, and the mixture was stirred at a temperature of 10°-15° C. for 1 hour. The reaction mixture was concentrated at room temperature, and the residue was purified by silica gel column chromatography (chloroform-methanol) to give 663 mg of N-[(2-oxo-1-pyrrolidinyl)acetyl]-L-prolyl-L-prolinal.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated at room temperature
  3. customthe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-148251ab3c6442518a4a15c8b8e4ab2f
Source dataset
uspto-grants-1992_06
Patent number
US05118811

Reaction notes

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