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 29333노트

반응식

HRID 29333 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-969832e9a53b4d5f8888c0607b4315d1
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420001B2

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