Acetone → 3(S)-(2,3-Dihydro-benzofuran-6-yl)-3-[2-oxo-3-(4-oxo-pentyl)-pyrrolidin-1-yl]-propionic acid ethyl ester

HRID 1108393Notes

Reaction equation

HRID 1108393 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH2:5][C@@H:6]([C:22]1[CH:30]=[CH:29][C:25]2[CH2:26][CH2:27][O:28][C:24]=2[CH:23]=1)[N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14][C:15]2([CH3:20])OCC[O:16]2)[C:8]1=[O:21])[CH3:2].CC1C=CC(S(O)(=O)=O)=CC=1.CC(C)=O>CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:31])[CH2:5][C@@H:6]([C:22]1[CH:30]=[CH:29][C:25]2[CH2:26][CH2:27][O:28][C:24]=2[CH:23]=1)[N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14][C:15](=[O:16])[CH3:20])[C:8]1=[O:21])[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 154537683(S)-(2,3-Dihydro-benzofuran-6-yl)-3-(3-[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-2-oxo-pyrrolidin-1-yl)-propionic acid ethyl ester

Product 1

HCID 154537693(S)-(2,3-Dihydro-benzofuran-6-yl)-3-[2-oxo-3-(4-oxo-pentyl)-pyrrolidin-1-yl]-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-1 (600 mg, 1.4 mmol), p-TSA (20 mg) and acetone (50 mL) was heated at reflux for 4 hr. The cooled reaction mixture was diluted with EtOAc and then washed with sat. NaHCO3 and brine, dried (MgSO4), and concentrated to afford 4-2 as a colorless oil.

Workup

  1. temperatureat reflux for 4 hr
  2. customThe cooled reaction mixture
  3. washwashed with sat. NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3a07463bccbd48839eae96aa3d8612f5
Source dataset
uspto-grants-2000_05
Patent number
US06066648

Reaction notes

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