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

HRID 2061043

反応式

HRID 2061043 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-ee26e2c2ed8b41c7b912640d4d442c61
出典データセット
uspto-grants-2012_10
特許番号
US08278482B2

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