Phosphate → 3-(R)-(4-fluoro-phenyl)-N-(6-formyl-1, 2,3,4-tetrahydro-naphthalen-2-(R)-yl)-3-(3-trifluoromethyl-benzenesulfonylamino)-propionamide

HRID 32125

反応式

HRID 32125 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:25][S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=2)(=[O:28])=[O:27])[CH2:9][C:10]([NH:12][C@@H:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH:23]=C)[CH:19]=3)[CH2:14]2)=[O:11])=[CH:4][CH:3]=1.C([OH:43])(C)(C)C.C1COCC1.O.C[N+]1([O-])CCOCC1.P([O-])([O-])([O-])=O>CCOC(C)=O.O=[Os](=O)(=O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:25][S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:36])[F:37])[CH:30]=2)(=[O:27])=[O:28])[CH2:9][C:10]([NH:12][C@@H:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH:23]=[O:43])[CH:19]=3)[CH2:14]2)=[O:11])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 1061PhosphateHCID 82029Methyl morpholine oxideHCID 22124471t-Butanol tetrahydrofuran waterHCID 689267513-(R)-(4-fluoro-phenyl)-3-(3-trifluoromethyl-benzenesulfonylamino)-N-(6-vinyl-1,2,3,4-tetrahydro-naphthalen-2-(R)-yl)-propionamide

生成物 1

HCID 865985073-(R)-(4-fluoro-phenyl)-N-(6-formyl-1, 2,3,4-tetrahydro-naphthalen-2-(R)-yl)-3-(3-trifluoromethyl-benzenesulfonylamino)-propionamide

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 3-(R)-(4-fluoro-phenyl)-3-(3-trifluoromethyl-benzenesulfonylamino)-N-(6-vinyl-1,2,3,4-tetrahydro-naphthalen-2-(R)-yl)-propionamide (314 mg, 0.575 mmol) in 13 mL of a mixture solvent t-butanol/THF/water (10:2:1) was added NMO (135 mg, 1.15 mmol), followed by OsO4 (2.5% w/w in t-butanol, 175 mg, 0.017 mmol). After stirring overnight at RT, 4 mL of pH=7.2 phosphate buffer was added, followed by NaIO4 (615 mg, 2.875 mmol). After stirring for 5 h at RT, the solution was diluted with EtOAc and washed with brine. The organic phase was dried over Na2SO4 and evaporated to dryness in vacuo. Flash chromatography (SiO2, EtOAc/hexane=1:1) afforded the desired compound as a white solid.

後処理

  1. stirringAfter stirring for 5 h at RT
  2. washwashed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated to dryness in vacuo

出典と根拠

ORDレコード
ord-b50a3d392710475188f34aa37375a1d3
出典データセット
uspto-grants-2008_09
特許番号
US07425631B2

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