Potassium trimethylsilanolate → (1R)-2-[(6-{4-[3-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

HRID 2118327Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2118327
[CH:1]1([S:6]([C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:30][C@@H:29]([C:31]4[CH:42]=[CH:41][C:34]5[O:35][C:36]([CH3:40])([CH3:39])[O:37][CH2:38][C:33]=5[CH:32]=4)[O:28]C3=O)[CH:12]=[CH:13][CH:14]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si](C)(C)[O-].[K+]>C1COCC1>[CH:1]1([S:6]([C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:30][C@@H:29]([C:31]3[CH:42]=[CH:41][C:34]4[O:35][C:36]([CH3:39])([CH3:40])[O:37][CH2:38][C:33]=4[CH:32]=3)[OH:28])[CH:12]=[CH:13][CH:14]=2)(=[O:8])=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

4

Edukt 2

HCID 23668039Potassium trimethylsilanolateHCID 69119376(5R)-3-(6-{4-[3-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Produkt 1

HCID 69119807(1R)-2-[(6-{4-[3-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred mixture of (5R)-3-(6-{4-[3-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one and potassium trimethyl silanolate (240 mg) in THF (6 ml) was heated to reflux for 1.5 h. The mixture was poured into phoshate buffer solution (pH 5) and extracted into DCM. The extracts were washed with water, dried (Na2SO4) and evaporated to give the title compound (120 mg). LCMS RT=2.93 min.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 h
  3. extractionextracted into DCM
  4. washThe extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-dffb7638fad8491c9a592050eb473ff8
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07442839B2

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