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 29333ノート

反応式

HRID 29333 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-969832e9a53b4d5f8888c0607b4315d1
出典データセット
uspto-grants-2008_09
特許番号
US07420001B2

反応ノート

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