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Carbon tetrabromide → N-[3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-(bromomethyl)phenyl]-N-propylmethanesulfonamide

HRID 899456
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HRID 899456 반응식
C[CH2:2][S:3]([N:6]([C:10]1[CH:15]=[C:14]([CH2:16]O)[CH:13]=[C:12]([CH2:18][O:19][CH2:20][C:21]([NH2:30])([CH3:29])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:11]=1)[CH2:7][CH2:8][CH3:9])(=[O:5])=[O:4].C(Br)(Br)(Br)[Br:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[NH2:30][C:21]([CH3:29])([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:20][O:19][CH2:18][C:12]1[CH:11]=[C:10]([N:6]([CH2:7][CH2:8][CH3:9])[S:3]([CH3:2])(=[O:5])=[O:4])[CH:15]=[C:14]([CH2:16][Br:32])[CH:13]=1
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참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67318200methyl N-[3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-(hydroxymethyl)phenyl]-N-propylmethanesulfonamide

생성물 1

HCID 67319075N-[3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-(bromomethyl)phenyl]-N-propylmethanesulfonamide

시약·촉매·용매 1

HCID 6344Dichloromethane
용매

실험 절차

To a solution of methyl N-[3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-(hydroxymethyl)phenyl]-N-propylmethanesulfonamide (140 mg, 0.269 mmol) in dichloromethane (2.5 mL) were added carbon tetrabromide (116 mg, 0.350 mmol) and triphenylphosphine (85.0 mg, 0.323 mmol). After 15 h, the reaction mixture was concentrated in vacuo and purified by flash chromatography (silica, 0-35% EtOAc/hexanes) to provide N-[3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-(bromomethyl)phenyl]-N-propylmethanesulfonamide as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.34 (s, 1H), 7.31 (s, 1H),), 7.30-7.20 (m, 4H), 7.18-7.14 (m, 2H), 4.60-4.50 (m, 3H), 4.49 (s, 2H), 3.64 (t, J=7.2 Hz, 2H), 3.55 (A of AB, d, J=8.7 Hz, 1H), 3.45 (B of AB, d, J=8.7 Hz, 1H), 3.14 (A of AB, d, J=13.3 Hz, 1H), 2.94 (B of AB, d, J=13.3 Hz, 1H), 2.88 (s, 3H), 1.56-1.47 (m, 2H), 1.46 (s, 9H), 1.27 (s, 3H), 0.91 (t, J=7.4 Hz, 3H).

후처리

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. custompurified by flash chromatography (silica, 0-35% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-a61e99680eb54a3288aded807b2d79b7
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07354942B2

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