Tetrahydrofuran → 2-[3-chloro-4-(methylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]propanoic acid

HRID 1881904Notes

Reaction equation

HRID 1881904 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:18][C@H:19]2[CH2:39][CH2:38][C:21]3([O:25][C@H:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C@@H:23]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[O:22]3)[CH2:20]2)[C:13]([O:15]CC)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].O1CCCC1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:18][C@H:19]2[CH2:39][CH2:38][C:21]3([O:22][C@H:23]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C@@H:24]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[O:25]3)[CH2:20]2)[C:13]([OH:15])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59331567ethyl 2-[3-chloro-4-(methylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]propanoate

Product 1

HCID 593314112-[3-chloro-4-(methylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]propanoic acidYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-[3-chloro-4-(methylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]propanoate in a mixed solvent of tetrahydrofuran (200 mL) and methanol (100 mL) was added 2M aqueous sodium hydroxide solution (50 mL), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure, the residue was acidified with 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-70:30, volume ratio) to give the title compound (17.6 g, yield 97%) as a colorless amorphous solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-70:30, volume ratio)

Sources & evidence

ORD record
ord-ef83317fe35f438d8b41f26bab55f2ce
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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