Water → 3-[(2S)-1-(3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-3-oxopropionic acid ethyl ester

HRID 1077883Notes

Reaction equation

HRID 1077883 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][CH:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:27])[CH2:14][CH2:15][C:16](=[O:26])[N:17]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:18])[OH:7])[CH3:2].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C.O>CC(C)=O>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:27])[CH2:14][CH2:15][C:16](=[O:26])[N:17]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:18])=[O:7])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 15660989(3RS)-3-[(2S)-1-(3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl)-3-hydroxypropionic acid ethyl esterHCID 131709961Jones' reagent

Product 1

HCID 156609903-[(2S)-1-(3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-3-oxopropionic acid ethyl esterYield 42.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of (3RS)-3-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propionyl]pyrrolidin-2-yl]-3-hydroxypropionic acid ethyl ester (230 mg) in acetone (1 ml) was cooled to -30° C. Excess Jones' reagent was added dropwise to the solution. The mixture was stirred for 1 hr at the same temperature, and for 1 hr at -20° C., and for 1 hr at -10° C. Isopropyl alcohol was added to the reaction solution. Water was added to the mixture. The mixture was extracted with EtOAc. The extract was washed, dried, and evaporated. The residue was purified by column chromatography on silica gel (hexane-EtOAc) to give the title compound (98 mg) having the following physical data:

Workup

  1. waitfor 1 hr at -20° C.
  2. waitfor 1 hr at -10° C
  3. extractionThe mixture was extracted with EtOAc
  4. washThe extract was washed
  5. customdried
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel (hexane-EtOAc)

Sources & evidence

ORD record
ord-fb5644d8286849648c72e49977b1e2e2
Source dataset
uspto-grants-1996_08
Patent number
US05545657

Reaction notes

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