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 29333Notes

Reaction equation

HRID 29333 reaction equation
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]

Participants

6

Reactant 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

Product 1

HCID 68715249methyl N-{[4'-({[4-(1,2-dihydroxyethyl)-3-methyl-1-benzofuran-2-yl]carbonyl}amino)-1,1'-biphenyl-4-yl]sulfonyl}-L-valinateYield 85.2%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-969832e9a53b4d5f8888c0607b4315d1
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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