Potassium Carbonate → HCID 68691453, 화합물

HRID 2238438노트

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HRID 2238438 반응식
[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]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 68692696HCID 68692696, 화합물

생성물 1

HCID 68691453HCID 68691453, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-302a65f1bed1452991ab5f8ea48c6a1f
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718688B2

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