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

HRID 344698Notes

Reaction equation

HRID 344698 reaction equation
CS(C)=O.[Cl-].[CH2:6]([N:13]([CH3:30])[C:14]([CH2:16][CH2:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[CH:25]([OH:29])[C:26]([OH:28])=[O:27])=[O:19])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:31](N(CC)CC)[CH3:32]>C(Cl)Cl.O>[CH2:31]([O:27][C:26](=[O:28])[C:25]([C@@H:21]1[CH2:22][CH2:23][CH2:24][N:20]1[C:18](=[O:19])[CH2:17][CH2:16][C:14](=[O:15])[N:13]([CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:30])=[O:29])[CH3:32]

Participants

7

Reactant 4

HCID 312ChlorideHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 15660980HCID 15660980, compound

Product 1

HCID 156609222-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-2-oxoacetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

DMSO (443 μl) was added dropwise to a solution of oxyalyl chloride (260 μl) in methylene chloride (10 ml) cooled to -78° C. The solution was stirred for 15 mins at the same temperature. A solution of (2RS)-2-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl]propanoyl]pyrrolidin-2-yl]-2-hydroxyacetic acid theyl ester (700 mg) in methylene chloride (6 ml) was added dropwise to the solution at the same temperature. The mixture was stirred for 20 mins. Triethylamine (1.42 ml) was added dropwise to the solution. The solution was stirred for 10 mins at the same temperature, and for 30 mins. at 0° C. Water was added to the reaction solution. 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 (627 mg) having the following physical data:

Workup

  1. stirringThe mixture was stirred for 20 mins
  2. stirringThe solution was stirred for 10 mins at the same temperature
  3. waitfor 30 mins
  4. customat 0° C
  5. extractionThe mixture was extracted with EtOAc
  6. washThe extract was washed
  7. customdried
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel (hexane-EtOAc)

Sources & evidence

ORD record
ord-8e2755fc563049288c08e13571093389
Source dataset
uspto-grants-1991_10
Patent number
US05053414

Reaction notes

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