Dimethyl Sulfoxide → HCID 15660982, compound

HRID 344701Notes

Reaction equation

HRID 344701 reaction equation
[CH2:1]([N:8]([CH3:25])[C:9]([CH2:11][CH2:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]([OH:24])[C:21]([OH:23])=[O:22])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CS(C)=O>O>[CH2:32]([O:22][C:21](=[O:23])[CH:20]([C@@H:16]1[CH2:17][CH2:18][CH2:19][N:15]1[C:13](=[O:14])[CH2:12][CH2:11][C:9](=[O:10])[N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:25])[OH:24])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 15660980HCID 15660980, compound

Product 1

HCID 15660982HCID 15660982, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (2RS)-2-[(2S)-1-[3-(N-benzyl-N-methlcarbamoyl)propanoyl]pyrrolidin-2-yl]-2-hydroxyacetic acid (134 mg), potassium carbonate (64 mg), benzyl bromide (51 μl) and DMSO (1 ml) was stirred for 1 hr at room temperature. Water was added to the mixture. The mixture was extracted with a mixture of hexane and EtOAc (1:1). The extract was washed, dried and evaporated. The residue was purified by column chromatography on silica gel (hexane-EtOAc) to give the title compound (141 mg) having the following physical data:

Workup

  1. extractionThe mixture was extracted with a mixture of hexane and EtOAc (1:1)
  2. washThe extract was washed
  3. customdried
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel (hexane-EtOAc)

Sources & evidence

ORD record
ord-b666ea103ec3465c8e15fc1ddebd04a4
Source dataset
uspto-grants-1991_10
Patent number
US05053414

Reaction notes

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