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

HRID 1848783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1848783
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:5]=[C:4]([CH3:16])[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][O:24][C:25]2[CH:37]=[CH:36][C:28]3[C@H:29]([CH2:32][C:33]([OH:35])=[O:34])[CH2:30][O:31][C:27]=3[CH:26]=2)[CH:18]=1.CC(C)=O>O>[OH2:8].[CH3:16][C:4]1[CH:5]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:7]=[C:2]([CH3:1])[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][O:24][C:25]2[CH:37]=[CH:36][C:28]3[C@H:29]([CH2:32][C:33]([OH:35])=[O:34])[CH2:30][O:31][C:27]=3[CH:26]=2)[CH:18]=1

Komponenten

4

Edukt 2

HCID 180AcetoneHCID 24857286Fasiglifam

Produkt 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 hydrateAusbeute 185,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To [(3S)-6-({2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid (15.0 g) were added acetone (30 mL) and water (10.5 mL) for dissolution therein. Activated carbon (0.45 g) was added, and the mixture was stirred at 45° C. for 10 min. The insoluble material was removed by filtration and washed with acetone (7.5 mL). Water (3 mL) was added dropwise to the filtrate, and the mixture was allowed to cool to room temperature. Seed crystal was added, and the mixture was stirred for 30 min. At 20° C., water (9 mL) and water (15 mL) was respectively added over 1 hr, and the mixture was stirred at 10° C. for 1 hr. The precipitated crystals were collected by filtration, and washed with a mixed solution (30 mL) of acetone.water (1:1) and then water (30 mL). The obtained crystals were dried at 30° C. under reduced pressure (1.5−3.0 kPa) to give [(3S)-6-({2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid hydrate as crystals (14.4 g). 100% ee.

Aufarbeitung

  1. dissolutionfor dissolution
  2. additionActivated carbon (0.45 g) was added
  3. customThe insoluble material was removed by filtration
  4. washwashed with acetone (7.5 mL)
  5. additionWater (3 mL) was added dropwise to the filtrate
  6. temperatureto cool to room temperature
  7. additionSeed crystal was added
  8. stirringthe mixture was stirred for 30 min
  9. additionAt 20° C., water (9 mL) and water (15 mL) was respectively added over 1 hr
  10. stirringthe mixture was stirred at 10° C. for 1 hr
  11. filtrationThe precipitated crystals were collected by filtration
  12. washwashed with a mixed solution (30 mL) of acetone
  13. customThe obtained crystals were dried at 30° C. under reduced pressure (1.5−3.0 kPa)

Quellen und Nachweise

ORD-Eintrag
ord-7fe03b12bf62466193bad13dfb72a812
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952185B2

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