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Benzoyl isothiocyanate → N-(((3S,4R,5S)-3-(2-fluorophenyl)-4-(hydroxymethyl)-5-(trifluoromethyl)tetrahydrofuran-3-yl)carbamothioyl)benzamide

HRID 1429611
ノート
印刷プレビュー

反応式

HRID 1429611 の反応式
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C@@:13]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[F:30])[CH2:17][O:16][C@H:15]([C:18]([F:21])([F:20])[F:19])[C@H:14]1[CH2:22][OH:23].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C@@:13]1([NH:12][C:10]([NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[S:11])[C@H:14]([CH2:22][OH:23])[C@@H:15]([C:18]([F:19])([F:20])[F:21])[O:16][CH2:17]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 68284Benzoyl isothiocyanateHCID 516892Sodium BicarbonateHCID 66869282((2S,3R,4S)-4-amino-4-(2-fluorophenyl)-2-(trifluoromethyl)tetrahydrofuran-3-yl)methanol

生成物 1

HCID 60169627N-(((3S,4R,5S)-3-(2-fluorophenyl)-4-(hydroxymethyl)-5-(trifluoromethyl)tetrahydrofuran-3-yl)carbamothioyl)benzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

実験手順

Benzoyl isothiocyanate (19.0 mL) was added to a solution containing ((2S,3R,45)-4-amino-4-(2-fluorophenyl)-2-(trifluoromethyl)tetrahydrofuran-3-yl)methanol (28.72 g) in DCM (150 mL), and the mixture was stirred at RT for 18 h. Sodium bicarbonate (sat., aq., 200 mL) was then added, the mixture extracted with EtOAc (3×300 mL), dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5% to 30% EtOAc in hexanes) to obtain the title compound (37.07 g). 1H-NMR (400 MHz, CDCl3) δ (ppm): 3.22 (dd, J=8.1, 4.5 Hz, 1 H), 3.31 (td, J=8.0, 3.0 Hz, 1 H), 3.94-4.07 (m, 1 H), 4.31-4.46 (m, 1 H), 4.53 (d, J=9.9 Hz, 1 H), 4.83 (d, J=9.9 Hz, 1 H), 6.97-7.14 (m, 1 H), 7.22 (td, J=7.7, 1.3 Hz, 1 H), 7.31-7.45 (m, 1 H), 7.49-7.61 (m, 2 H), 7.61-7.70 (m, 1 H), 7.75 (td, J=8.1, 1.5 Hz, 1 H), 7.79-7.93 (m, 2 H), 8.90 (s, 1 H), 11.85 (s, 1 H)

後処理

  1. extractionthe mixture extracted with EtOAc (3×300 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (5% to 30% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-ebe0ffce09ad411090b0924213acf8cf
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08940734B2

反応ノート

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