Water → HCID 54319933, compound

HRID 1263278Notes

Reaction equation

HRID 1263278 reaction equation
[OH:1][C:2]([CH3:27])([C:20]([F:26])([F:25])[CH2:21][CH2:22][CH2:23][CH3:24])[CH:3]=[CH:4][CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][CH:12]([OH:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:29].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>CN(C)C=O>[OH:1][C:2]([CH3:27])([C:20]([F:26])([F:25])[CH2:21][CH2:22][CH2:23][CH3:24])[CH:3]=[CH:4][CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:29])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 54337876HCID 54337876, compound

Product 1

HCID 54319933HCID 54319933, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 19 (37 mg, 0.09 mmol) in dimethylformamide (1 mL) containing pyridinium dichromate (165 mg, 0.45 mmol) was stirred at room temperature overnight. It was then poured into water and extracted with ether three times. The combined ether layer was washed with water and dried over magnesium sulfate. Removal of the solvent in vacuo gave 11.6 mg of 7-[2-(3-hydroxy-3-methyl-4,4-difluoro-1-octen-1-yl)-5- oxopyrrolidin-1-yl]-6-oxo-heptanoic acid (20). IR (CH2Cl2): 3600-2800 (br), 1730, 1690 cm-1 ; PMR (CDCl3); δ5.85-5.62 (m, 2H), 4.33-3.65 (m, 3H), 2.50-1.20 (m, 21H), and 0.92 (t, 3H); MS: m/z 385.2048 (M+ --H2O), calcd. for C20H29NO4F2, 385.2064.

Workup

  1. extractionextracted with ether three times
  2. washThe combined ether layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-916262cc001c4b038661fcc3f2b932dc
Source dataset
uspto-grants-1984_06
Patent number
US04456613

Reaction notes

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