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

HRID 2238399

反応式

HRID 2238399 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-303824f700934af7a3f54a2518379247
出典データセット
uspto-grants-2010_05
特許番号
US07718688B2

関連ノート

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