N-bromobutanimide → Methyl 2-[(tert-butoxycarbonyl)amino]-1-bromo-6-naphthoate

HRID 2238399

반응식

HRID 2238399 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]([O:21][CH3:22])=[O:20])[CH:13]=[CH:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:30])C(=O)C1>CC#N>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]([O:21][CH3:22])=[O:20])[CH:15]=2)[C:10]=1[Br:30])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 44549532Methyl 6-[(tert-butoxycarbonyl)amino]-2-naphthoate

생성물 1

HCID 44549919Methyl 2-[(tert-butoxycarbonyl)amino]-1-bromo-6-naphthoate수율 91%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of ester 147 (977 mg, 3.24 mmol) and NBS (664 mg, 3.73 mmol) in CH3CN (25 mL) was stirred at reflux for 45 min, then concentrated under reduced pressure. The residue was dissolved in CH2Cl2 and the solution was washed with 10% aqueous Na2SO3 and water (×2), dried, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with CH2Cl2, to give methyl 2-[(tert-butoxycarbonyl)amino]-1-bromo-6-naphthoate (148) (1.12 g, 91%) as a white solid: mp (petroleum ether) 130-131° C.; 1H NMR [(CD3)2SO] δ 8.93 (s, 1H), 8.65 (d, J=1.6 Hz, 1H), 8.64 (d, J=8.9 Hz, 1H), 8.16 (d, J=8.9 Hz, 1H), 8.11 (dd, J=8.9, 1.7 Hz, 1H), 7.86 (d, J=8.9 Hz, 1H), 3.93 (s, 3H), 1.50 (s, 9H). Anal. (C17H18BrNO4) C, H, N, Br.

후처리

  1. temperatureat reflux for 45 min
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washthe solution was washed with 10% aqueous Na2SO3 and water (×2)
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel
  8. washeluting with CH2Cl2

출처 및 근거

ORD 기록
ord-303824f700934af7a3f54a2518379247
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718688B2

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