Water → 4-Methoxybenzoic acid, 6-aminohexyl ester

HRID 1743486노트

반응식

HRID 1743486 반응식
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]=[N+]=[N-])=[O:8])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[O:8])=[CH:19][CH:20]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 865836674-Methoxybenzoic acid, 6-azidohexyl ester

생성물 1

HCID 572173864-Methoxybenzoic acid, 6-aminohexyl ester수율 78%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 4-methoxybenzoic acid, 6-azidohexyl ester (1.119 g, 4.035 mmol), triphenylphosphine (1.164 g, 4.439 mmol), and water (0.08 ml) in THF was stirred under nitrogen at room temperature. After ˜144 h, the reaction mixture was diluted with EtOAc (50 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The residue was purified by flash chromatography (2×)(alumina, chloroform to 10% MeOH/CHCl3 gradient) to give the desired product as a light yellow oil (0.0796 g, 78%); 1H NMR (400 MHz, DMSO-d6) δ 1.18–1.40 (m, 6H), 1.63–1.71 (m, 2H), 2.50 (t, J=6.4 Hz, 2H), 3.82 (s, 3H), 4.21 (t, J=6.6 Hz, 2H), 7.01–7.06 (m, 2H), 7.87–7.92 (m, 2H); IR (KBr) 3410 (broad), 2940, 1710, 1605, 1510, 1260 cm−1; mass spectrum [(+)ESI], m/z 252 (M+H)+.

후처리

  1. dry with materialdried over Na2SO4
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated in vac
  4. customdried
  5. customThe residue was purified by flash chromatography (2×)(alumina, chloroform to 10% MeOH/CHCl3 gradient)

출처 및 근거

ORD 기록
ord-5f2a41d184424fb881bc795d93002616
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07008636B2

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