Methyl iodide → 1-(2-(3-(Benzyloxycarbonylamino)-3-methylbutanoyloxy)ethyl)-1-methylpiperidinium iodide

HRID 2061043

반응식

HRID 2061043 반응식
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:26])([CH3:25])[CH2:13][C:14]([O:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][I:28]>ClCCl>[I-:28].[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:26])([CH3:25])[CH2:13][C:14]([O:16][CH2:17][CH2:18][N+:19]1([CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 6328Methyl iodideHCID 601344582-(Piperidin-1-yl)ethyl 3-(benzyloxycarbonylamino)-3-methylbutanoate

생성물 1

HCID 673106161-(2-(3-(Benzyloxycarbonylamino)-3-methylbutanoyloxy)ethyl)-1-methylpiperidinium iodide수율 66.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A batch of 2-(piperidin-1-yl)ethyl 3-(benzyloxycarbonylamino)-3-methylbutanoate (9.45 g, 26.1 mmol) was dissolved in a solution of dichloromethane (40 ml) and methyl iodide (16.3 ml, 262 mmole). The mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo, and the crude material was purified by pre-HPLC to give 8.74 g (66%) of 1-(2-(3-(benzyloxycarbonylamino)-3-methylbutanoyloxy)ethyl)-1-methylpiperidinium iodide. 1H NMR (CD3OD) δ 7.39-7.27 (m, 5 H), 5.05 (s, 2 H), 4.52-4.47 (m, 2 H), 3.70-3.64 (m, 2 H), 3.44-3.37 (m, 4 H), 3.09 (s, 3 H), 2.84 (s, 2 H), 1.92-1.86 (m, 4 H), 1.73-1.59 (m, 2 H), 1.39 (s, 6 H). MS (ESI+) calculated for C21H33N2O4+: 377.24, Found: 377.2 (M+).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude material was purified by pre-HPLC

출처 및 근거

ORD 기록
ord-ee26e2c2ed8b41c7b912640d4d442c61
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278482B2

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