Potassium Carbonate → HCID 68691453、化合物

HRID 2238438ノート

反応式

HRID 2238438 の反応式
[CH2:1]([N:8]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[S:9]([C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:19]2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([Br:44])C(=O)C1.C([O-])([O-])=O.[K+].[K+]>CC#N>[Br:44][C:19]1[C:20]2[C:15](=[CH:14][CH:13]=[C:12]([S:9]([N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)(=[O:11])=[O:10])[CH:21]=2)[CH:16]=[CH:17][C:18]=1[NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 68692696HCID 68692696、化合物

生成物 1

HCID 68691453HCID 68691453、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
40 °C

実験手順

A mixture of 211 (1.15 g, 2.29 mmol), NBS (450 mg, 2.52 mmol), and K2CO3 (380 mg, 2.75 mmol) in MeCN (25 mL) was stirred at 40° C. under nitrogen for 30 min. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and H2O. The EtOAc layer was washed with H2O, brine, then dried and evaporated. The residue was recrystallised from EtOAc/Et2O/petroleum ether to give tert-butyl 1-bromo-7-[(dibenzylamino)sulfonyl]-2-naphthylcarbamate (212) as colorless crystals: mp 150-151° C.; 1H NMR (CDCl3) δ 8.69 (d, J=1.6 Hz, 1H), 8.57 (d, J=9.1 Hz, 1H), 7.89 (d, J=8.6 Hz, 1H), 7.85 (d, J=9.1 Hz, 1H), 7.74 (dd, J=8.6, 1.8 Hz, 1H), 7.38 (s, 1H), 7.22-7.15 (m, 6H), 7.12-7.05 (m, 4H), 4.40 (s, 4H), 1.58 (s, 9H); 13C NMR δ 152.4, 139.6, 136.5, 135.5, 132.0, 131.5, 129.7, 128.6, 128.5, 128.1, 127.7, 126.8, 122.1, 121.8, 110.4, 81.8, 50.6, 28.3. Anal. (C29H29BrN2O4S) C, H, N.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and H2O
  3. washThe EtOAc layer was washed with H2O, brine
  4. customdried
  5. customevaporated
  6. customThe residue was recrystallised from EtOAc/Et2O/petroleum ether

出典と根拠

ORDレコード
ord-302a65f1bed1452991ab5f8ea48c6a1f
出典データセット
uspto-grants-2010_05
特許番号
US07718688B2

反応ノート

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