Potassium Carbonate → 3-hydroxy-5-[(1R)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 20575ノート

反応式

HRID 20575 の反応式
I[Si](C)(C)C.[OH:6][C:7]1[CH:8]=[C:9]([CH:19]=[C:20]([O:22][C@H:23]([CH3:27])[CH2:24][O:25]C)[CH:21]=1)[C:10]([NH:12][C:13]1[CH:17]=[CH:16][N:15]([CH3:18])[N:14]=1)=[O:11].C(=O)([O-])[O-].[K+].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.CO>[OH:6][C:7]1[CH:8]=[C:9]([CH:19]=[C:20]([O:22][C@H:23]([CH3:27])[CH2:24][OH:25])[CH:21]=1)[C:10]([NH:12][C:13]1[CH:17]=[CH:16][N:15]([CH3:18])[N:14]=1)=[O:11]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 593469263-hydroxy-5-[(1R)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

生成物 1

HCID 593468763-hydroxy-5-[(1R)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide収率 64%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒

実験手順

Iodotrimethylsilane (6.64 mL, 47 mmol) was added to a solution of 3-hydroxy-5-[(1R)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (2.86 g, 9.38 mmol) in acetonitrile (120 mL) and the resultant mixture stirred for 24 hours. Methanol (30 mL) was added and the mixture stirred for 30 minutes, saturated potassium carbonate (30 mL) and saturated sodium thiosulphate (30 mL) were then added and the mixture stirred for 20 mins. The acetonitrile was removed in vacuo and water (50 mL) added. The mixture was adjusted to pH4 with 1M hydrochloric acid, extracted into ethyl acetate (3×100 mL) and the combined extracts washed with brine (50 mL), dried (MgSO4) and evaporated to a residue which was chromatographed on silica, eluting with a gradient of 0-50% methanol in ethyl acetate, to give the desired compound (1.75 g).

後処理

  1. stirringthe mixture stirred for 20 mins
  2. customThe acetonitrile was removed in vacuo and water (50 mL)
  3. additionadded
  4. extractionextracted into ethyl acetate (3×100 mL)
  5. washthe combined extracts washed with brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated to a residue which
  8. customwas chromatographed on silica
  9. washeluting with a gradient of 0-50% methanol in ethyl acetate

出典と根拠

ORDレコード
ord-c915cfb25161492b96e2997f6cc8dfc9
出典データセット
uspto-grants-2010_06
特許番号
US07745475B2

反応ノート

読み込み中…