Hydrochloric Acid → (3RS)-3-[(2S)-1-(3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl)-3-hydroxypropionic acid ethyl ester

HRID 344703Notes

Reaction equation

HRID 344703 reaction equation
II.Br[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:10]([N:17]([CH3:31])[C:18]([CH2:20][CH2:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][C@H:25]1[CH:29]=[O:30])=[O:23])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>C1COCC1.C1C=CC=CC=1.[Zn]>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][CH:29]([C@@H:25]1[CH2:26][CH2:27][CH2:28][N:24]1[C:22](=[O:23])[CH2:21][CH2:20][C:18](=[O:19])[N:17]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:31])[OH:30])[CH3:9]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 7748Ethyl bromoacetateHCID 14674666(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-al

Product 1

HCID 15660989(3RS)-3-[(2S)-1-(3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl)-3-hydroxypropionic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Zinc powder (482 mg) and a small amount of iodine were added to a solution of ethyl bromoacetate (0.70 ml) in THF (6 ml). The mixture was refluxed for 30 mins. The solution was added dropwise to a solution of (2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-al (1.21 g) in benzene (10 ml). The mixture was refluxed for 30 mins. After reaction, 1N hydrochloric acid 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 (1.21 g) having the following physical data:

Workup

  1. temperatureThe mixture was refluxed for 30 mins
  2. temperatureThe mixture was refluxed for 30 mins
  3. additionwas added to the mixture
  4. extractionThe mixture was extracted with EtOAc
  5. washThe extract was washed
  6. customdried
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel (hexane-EtOAc)

Sources & evidence

ORD record
ord-b30ad46a94c54985b6aecece104c43f9
Source dataset
uspto-grants-1991_10
Patent number
US05053414

Reaction notes

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