Methanol → HCID 59570904, compound

HRID 2192906Notes

Reaction equation

HRID 2192906 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([CH:16]([CH2:21][C@H:22]3[CH2:42][CH2:41][C:24]4([O:28][C@H:27]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C@@H:26]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[O:25]4)[CH2:23]3)[C:17]([O:19]C)=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH2:3][CH2:2]1.[OH-].[Na+].CO>C1COCC1>[CH:1]1([C:4]2[CH:5]=[C:6]([CH:16]([CH2:21][C@H:22]3[CH2:42][CH2:41][C:24]4([O:28][C@H:27]([C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)[C@@H:26]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[O:25]4)[CH2:23]3)[C:17]([OH:19])=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:14][CH2:15]2)(=[O:12])=[O:11])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59571057HCID 59571057, compound

Product 1

HCID 59570904HCID 59570904, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]propionate (66.5 g), 4 M aqueous sodium hydroxide solution (66.5 mL), methanol (66.5 mL), and THF (133 mL) was stirred under heating and reflux for 30 minutes, and left to be cooled at room temperature, and the organic solvent was evaporated under reduced pressure. To the residue was added chloroform (500 mL), and concentrated hydrochloric acid (25 mL) was then added thereto under ice-cooling. The organic layer was washed with saturated brine (200 mL×2) and dried over anhydrous sodium sulfate, and the solvent was then evaporated under reduced pressure to obtain 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]propionic acid (64.8 g) as an off-white amorphous substance.

Workup

  1. temperatureunder heating
  2. temperaturereflux for 30 minutes
  3. waitleft
  4. customthe organic solvent was evaporated under reduced pressure
  5. additionTo the residue was added chloroform (500 mL), and concentrated hydrochloric acid (25 mL)
  6. additionwas then added
  7. temperatureunder ice-cooling
  8. washThe organic layer was washed with saturated brine (200 mL×2)
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-214511dc162a4506b68c086baed8c5a1
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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