Dimethyl Sulfoxide → HCID 22862589, compound

HRID 1735418Notes

Reaction equation

HRID 1735418 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH:11]([C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:19])[OH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CS(C)=O.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Si:1]([O:8][CH2:9][CH2:10][C:11]([C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25]([NH:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])=[O:19])=[O:12])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 67745419HCID 67745419, compound

Product 1

HCID 22862589HCID 22862589, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A sulfur trioxide-pyridine complex (985 mg) was added to a solution of (S)-2-[[(S)-2-[3-(tert-butyldimethylsilyloxy)-1-hydroxypropyl]-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide (1.01 g) in a mixture of toluene (2 ml), DMSO (3 ml) and triethyl amine (0.94 ml), under ice-cooling, and the mixture was stirred for 3 hours. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with 10% citric acid, water, saturated sodium hydrogencarbonate, 1% hypochlorous acid, and water in order, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (eluent: chloroform-methanol) to give (S)-2[[(S)-2-[3-(tert-butyldimethylsilyloxy)-1-oxopropyl]-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide (374 mg) and the title compound (280 mg) (see Table 5).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 10% citric acid, water, saturated sodium hydrogencarbonate, 1% hypochlorous acid, and water in order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e5f2f801e5164a3a934443de65604dc5
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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