Water → 3-Bromo-6-{[(tert-butoxy)carbonyl]amino}-2-methylbenzoic acid

HRID 1725882ノート

反応式

HRID 1725882 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:10]=1[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br-:19].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.O>CN(C=O)C>[Br:19][C:15]1[C:14]([CH3:18])=[C:10]([C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:17][CH:16]=1)[C:11]([OH:13])=[O:12]

参加物

5

反応物 3

HCID 962WaterHCID 222451232-((tert-Butoxycarbonyl)amino)-6-methylbenzoic acidHCID 23500184Tetra-n-butylammonium tribromide

生成物 1

HCID 688664473-Bromo-6-{[(tert-butoxy)carbonyl]amino}-2-methylbenzoic acid収率 88.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of Example 104A (10 g, 40 mmol) and tetrabutylammonium tribromide (19.2 g, 40 mmol) in DMF (250 mL) was treated slowly with water (250 mL). The resulting suspension was stirred for 18 hours and partitioned between water (1.2 L) and ethyl acetate (500 mL). The organic layer was washed with water (2×1 L), dried (Na2SO4), filtered, and concentrated. The residue was dissolved in dichloromethane (900 mL), washed with water (5×1 L) and brine, dried (Na2SO4), filtered, and concentrated to provide the desired product (11.7 g). MS (ESI(−)) m/e 328, 330 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 13.60 (br s, 1H), 9.68 (s, 1H), 7.63 (d, 1H), 7.39 (d, 1H), 2.37 (s, 3H), 1.44 (s, 9H).

後処理

  1. custompartitioned between water (1.2 L) and ethyl acetate (500 mL)
  2. washThe organic layer was washed with water (2×1 L)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in dichloromethane (900 mL)
  7. washwashed with water (5×1 L) and brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-184c9bdfbf784ffe92c977493bde5054
出典データセット
uspto-grants-2009_02
特許番号
US07491718B2

反応ノート

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