Hydrochloric Acid → [(3S)-6-({4'-[(4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methoxy]-2',6'-dimethylbiphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid

HRID 416182Notes

Reaction equation

HRID 416182 reaction equation
C[O:2][C:3](=[O:41])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][CH2:15][C:16]3[CH:17]=[C:18]([C:22]4[C:27]([CH3:28])=[CH:26][C:25]([O:29][CH2:30][C:31]5([OH:39])[CH2:36][CH2:35][S:34](=[O:38])(=[O:37])[CH2:33][CH2:32]5)=[CH:24][C:23]=4[CH3:40])[CH:19]=[CH:20][CH:21]=3)=[CH:13][C:8]=2[O:7][CH2:6]1.CO.[OH-].[Na+].Cl>O.O1CCCC1>[OH:39][C:31]1([CH2:30][O:29][C:25]2[CH:26]=[C:27]([CH3:28])[C:22]([C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([CH2:15][O:14][C:12]4[CH:11]=[CH:10][C:9]5[C@H:5]([CH2:4][C:3]([OH:41])=[O:2])[CH2:6][O:7][C:8]=5[CH:13]=4)[CH:17]=3)=[C:23]([CH3:40])[CH:24]=2)[CH2:32][CH2:33][S:34](=[O:37])(=[O:38])[CH2:35][CH2:36]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 57414805HCID 57414805, compound

Product 1

HCID 24857285[(3S)-6-({4'-[(4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methoxy]-2',6'-dimethylbiphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acidYield 76.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl[(3S)-6-({4′-[(4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methoxy]-2′,6′-dimethylbiphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetate (0.482 g, 0.830 mmol) in a mixed solvent of methanol (2 mL) and tetrahydrofuran (4 mL) was added 2 M aqueous sodium hydroxide solution (1 mL), and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was diluted with water, acidified with 1 M hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The precipitated crystals were recrystallized from heptane-ethyl acetate to give the title compound (0.358 g, yield 76%) as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe precipitated crystals were recrystallized from heptane-ethyl acetate

Sources & evidence

ORD record
ord-fedda8cac44f4fb4aa0ba55e7bff253b
Source dataset
uspto-grants-2012_01
Patent number
US08088821B2

Reaction notes

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