[(3S)-6-({2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid hydrate → [(3S)-6-({2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid anhydride

HRID 1848785Notes

Reaction equation

HRID 1848785 reaction equation
[OH2:1].[CH3:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:6]=[C:5]([CH3:17])[C:4]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][O:25][C:26]2[CH:38]=[CH:37][C:29]3[C@H:30]([CH2:33][C:34]([OH:36])=[O:35])[CH2:31][O:32][C:28]=3[CH:27]=2)[CH:19]=1>CC(O)C>[CH3:17][C:5]1[CH:6]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:8]=[C:3]([CH3:2])[C:4]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][O:25][C:26]2[CH:38]=[CH:37][C:29]3[C@H:30]([CH2:33][C:34]([O:36][C:34](=[O:35])[CH2:33][C@H:30]4[C:29]5[CH:28]=[CH:27][C:26]([O:25][CH2:24][C:20]6[CH:19]=[C:18]([C:4]7[C:5]([CH3:17])=[CH:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:14])=[O:15])=[CH:8][C:3]=7[CH3:2])[CH:23]=[CH:22][CH:21]=6)=[CH:38][C:37]=5[O:1][CH2:31]4)=[O:35])[CH2:31][O:32][C:28]=3[CH:27]=2)[CH:19]=1

Participants

3

Reactant 1

HCID 46869922[(3S)-6-({2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid hydrate

Product 1

HCID 86706790[(3S)-6-({2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid anhydride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
55 °C

Procedure

[(3S)-6-({2′,6′-Dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid hydrate (0.5 hydrate) (100 mg) was dissolved in 2-propanol (2.5 mL) at 55° C. After filtration, n-heptane (2.5 mL) heated to 55° C. was added, and the mixture was allowed to gradually cool to 5° C. with stirring. The precipitated crystals were collected by filtration to give [(3S)-6-({2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid anhydride as crystals (A form crystal) (about 60 mg).

Workup

  1. filtrationAfter filtration, n-heptane (2.5 mL)
  2. additionwas added
  3. temperatureto gradually cool to 5° C.
  4. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-8e583e766bd84987b32e153ede73d9cf
Source dataset
uspto-grants-2015_02
Patent number
US08952185B2

Reaction notes

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