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

HRID 1725882노트

반응식

HRID 1725882 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-184c9bdfbf784ffe92c977493bde5054
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491718B2

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