Dimethyl Sulfoxide → HCID 22862580, compound

HRID 1735408Notes

Reaction equation

HRID 1735408 reaction equation
[OH:1][CH:2]([C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([C@@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:24](=[O:35])[CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=[O:18])[CH2:3][O:4]CC1C=CC=CC=1.C1(C)C=CC=CC=1.CS(C)=O>C(N(CC)CC)C>[OH:4][CH2:3][C:2]([C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([C@@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:24](=[O:35])[CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=[O:18])=[O:1]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 1140TolueneHCID 67745418HCID 67745418, compound

Product 1

HCID 22862580HCID 22862580, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A sulfur trioxide-pyridine complex (716 mg) was added, under ice-cooling, to a solution of (S)-2-[[(S)-2-(1-hydroxy-2(phenylmethyloxy)ethyl]-1-pyrrolidinyl]carbonyl]-1-[(4methoxyphenyl)oxyacetyl]pyrrolidine (988 mg) in a mixed solvent of toluene (1 ml), DMSO (1.5 ml) and triethylamine (0.7 ml) and the mixture was stirred for 2.5 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with a 10% aqueous solution of citric acid, saturated sodium hydrogencarbonate and water in order, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluent: chloroform-methanol) to give the title compound (673 mg).

Workup

  1. additionA sulfur trioxide-pyridine complex (716 mg) was added, under ice-
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with a 10% aqueous solution of citric acid, saturated sodium hydrogencarbonate and water in order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (eluent: chloroform-methanol)

Sources & evidence

ORD record
ord-02a26f460bfe44ac959099f7ca1103b8
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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