Water → methyl N-{[4'-({[4-(1,2-dihydroxyethyl)-3-methyl-1-benzofuran-2-yl]carbonyl}amino)-1,1'-biphenyl-4-yl]sulfonyl}-L-valinate

HRID 29333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 29333
C[N+]1([O-])CC[O:5]CC1.[CH3:9][C:10]1[C:14]2[C:15]([CH:19]=[CH2:20])=[CH:16][CH:17]=[CH:18][C:13]=2[O:12][C:11]=1[C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([S:36]([NH:39][C@H:40]([C:44]([O:46][CH3:47])=[O:45])[CH:41]([CH3:43])[CH3:42])(=[O:38])=[O:37])=[CH:32][CH:31]=2)=[CH:26][CH:25]=1)=[O:22].[OH2:48]>C1COCC1.[Os](=O)(=O)(=O)=O>[OH:48][CH:19]([C:15]1[C:14]2[C:10]([CH3:9])=[C:11]([C:21]([NH:23][C:24]3[CH:25]=[CH:26][C:27]([C:30]4[CH:35]=[CH:34][C:33]([S:36]([NH:39][C@H:40]([C:44]([O:46][CH3:47])=[O:45])[CH:41]([CH3:43])[CH3:42])(=[O:38])=[O:37])=[CH:32][CH:31]=4)=[CH:28][CH:29]=3)=[O:22])[O:12][C:13]=2[CH:18]=[CH:17][CH:16]=1)[CH2:20][OH:5]

Komponenten

6

Edukt 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 68714271methyl N-[(4'-{[(3-methyl-4-vinyl-1-benzofuran-2-yl)carbonyl]amino}-1,1'-biphenyl-4-yl)sulfonyl]-L-valinate

Produkt 1

HCID 68715249methyl N-{[4'-({[4-(1,2-dihydroxyethyl)-3-methyl-1-benzofuran-2-yl]carbonyl}amino)-1,1'-biphenyl-4-yl]sulfonyl}-L-valinateAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of N-methyl morpholine-N-oxide (50% wt solution in water, 0.103 g, 0.44 mmol) in THF and water (1 mL/0.3 mL) was added 0.096 mL (0.38 mmol) of osmium tetroxide (2.5 wt % in t-butanol). To that solution was quickly added 0.21 g (0.38 mmol) of methyl N-[(4′-{[(3-methyl-4-vinyl-1-benzofuran-2-yl)carbonyl]amino}-1,1′-biphenyl-4-yl)sulfonyl]-L-valinate (Example 96, Step 2). The reaction was stirred at room temperature for 2 hours and then quenched with excess sodium hydrosulfite in water. The reaction mixture was extracted with ethyl acetate and water. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated to provide 0.19 g of methyl N-{[4′-({[4-(1,2-dihydroxyethyl)-3-methyl-1-benzofuran-2-yl]carbonyl}amino)-1,1′-biphenyl-4-yl]sulfonyl}-L-valinate. Yield 85.2%. m.p. 90-95° C. MS: 581.2 (M+H)+.

Aufarbeitung

  1. customquenched with excess sodium hydrosulfite in water
  2. extractionThe reaction mixture was extracted with ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-969832e9a53b4d5f8888c0607b4315d1
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420001B2

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