Benzyl Bromide → HCID 21056496, 화합물

HRID 2215863노트

반응식

HRID 2215863 반응식
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:6][C:5]=1[N+:18]([O-])=O.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:6][C:5]=1[NH2:18]

참가 물질

4

반응물 2

HCID 7498Benzyl BromideHCID 69034741HCID 69034741, 화합물

생성물 1

HCID 21056496HCID 21056496, 화합물수율 57.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of CsCO3 (4.9 g, 15 mmoles) and (4-tert-Butoxycarbonylamino-2-nitro-benzoic acid methyl ester (2.96 g, 10 mmoles) in anhydrous DMF (100 mL) was added benzyl bromide (2.57 g, 15 mmoles) and the resulting mixture was stirred at room temperature for 12 hrs. The reaction mixture was filtered, concentrated, diluted with ethyl acetate, and washed with 5% citric acid, saturated NaHCO3 solution and water. The organic phase was hydrogenated over 10% Pd/C in EtOAc. After 12 hr, the mixture was filtered through a celite pad, and the filtrate was concentrated in vacuo to give a crude oil which was purified by column chromatography to furnish the desired product as an off-white solid (2.05 g, 57% yield). ES+ MS showed 357 m/z, the correct mass for the product. 1H NMR (400 MHz, DMSO-d6) showed β=1.34 (s, 9H), 3.71 (s, 3H), 4.74 (s, 2H), 6.39 (d, J=9 Hz, 1H), 6.62 (s, 1+2H), 7.19 (d, J=7 Hz, 2H), 7.24 (d, J=7 Hz, 1H), 7.32 (dd, J1=J2=7 Hz, 2H),.

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with 5% citric acid, saturated NaHCO3 solution and water
  5. waitAfter 12 hr
  6. filtrationthe mixture was filtered through a celite pad
  7. concentrationthe filtrate was concentrated in vacuo
  8. customto give a crude oil which
  9. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-602542bea0f245588017a8aa23f59d4c
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109332B2

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