Acetic Acid → HCID 59423435、化合物

HRID 1365022

反応式

HRID 1365022 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[CH3:10][C:11]([CH3:18])([CH3:17])[C:12](=O)[C:13]([OH:15])=[O:14].C(O)(=O)C.[B-]C#N.[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][CH:12]([C:11]([CH3:18])([CH3:17])[CH3:10])[C:13]([OH:15])=[O:14])[CH:7]=[CH:8][CH:9]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 108243-MethoxyanilineHCID 13150Trimethylpyruvic acidHCID 20587905Sodium cyanoborohydride [MI]

生成物 1

HCID 59423435HCID 59423435、化合物収率 16%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a mixture of 3-methoxyaniline (100 mg, 0.812 mmol) and trimethylpyruvic acid (211 mg, 1.624 mmol) in methanol (3 mL) at rt was added acetic acid (0.930 mL, 16.24 mmol). The mixture was stirred for 30 min at rt then heated at 70° C. for 2 hrs. The mixture was cooled down to rt before adding sodium cyanotrihydroborate (1.624 mL, 1.624 mmol). The mixture was stirred overnight at rt. Water (10 mL) was added, and the mixture was extracted with ethyl acetate (3×10 mL). The organic layer was washed with sat. NaHCO3 and brine solution, and then dried over Na2SO4, filtered, and evaporated to dryness. The residue was purified by preparative HPLC to get a white solid (30.5 mg, 16%) as product.

後処理

  1. temperaturethen heated at 70° C. for 2 hrs
  2. temperatureThe mixture was cooled down to rt
  3. stirringThe mixture was stirred overnight at rt
  4. extractionthe mixture was extracted with ethyl acetate (3×10 mL)
  5. washThe organic layer was washed with sat. NaHCO3 and brine solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-8b2252f6b0b145209cd06fcde3d55936
出典データセット
uspto-grants-2011_02
特許番号
US07888464B2

関連ノート

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