Isobutyl carbamate → HCID 21877961、化合物

HRID 1991272ノート

反応式

HRID 1991272 の反応式
[S:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:12]([F:13])=[CH:11][C:10]([NH2:14])=[CH:9][C:8]=2[F:15])[CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].[C:21](=[O:28])([O:23][CH2:24][CH:25]([CH3:27])[CH3:26])N>C1COCC1.O>[CH2:24]([O:23][C:21](=[O:28])[NH:14][C:10]1[CH:9]=[C:8]([F:15])[C:7]([C:4]2[CH2:5][CH2:6][S:1][CH2:2][CH:3]=2)=[C:12]([F:13])[CH:11]=1)[CH:25]([CH3:27])[CH3:26]

参加物

5

反応物 3

HCID 10973Isobutyl carbamateHCID 516892Sodium BicarbonateHCID 21876582HCID 21876582、化合物

生成物 1

HCID 21877961HCID 21877961、化合物

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

To a stirred, biphasic mixture of 4-(3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorobenzenamine (Step 4, 3.90 g, 17.2 mmol) in THF/water (2:1, 103 mL) is added sodium bicarbonate (2.88 g, 34.3 mmol) followed by isobutyl carbamate (2.45 mL, 18.9 mmol) dropwise. The reaction mixture is stirred at ambient temperature for 7 h and is then concentrated under reduced pressure, diluted with EtOAc (100 mL) and H2O (50 mL), and the layers are separated. The organic phase is washed with H2O (25 mL) and saline (25 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Purification of the residue by chromatography on a Biotage Flash 40M 90 g silica gel cartridge, eluting with 5-10% EtOAc/Hexanes, affords the title compound, mp 136-137° C.; MS (ESI−) for C16H19F2NO2S m/z 326 (M−H)−.

後処理

  1. concentrationis then concentrated under reduced pressure
  2. additiondiluted with EtOAc (100 mL) and H2O (50 mL)
  3. customthe layers are separated
  4. washThe organic phase is washed with H2O (25 mL) and saline (25 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the residue by chromatography on a Biotage Flash 40M 90 g silica gel cartridge
  8. washeluting with 5-10% EtOAc/Hexanes

出典と根拠

ORDレコード
ord-5ccce4c5b8cd4c2fa1c395de2c10c357
出典データセット
uspto-grants-2010_01
特許番号
US07645781B2

反応ノート

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