Formic Acid → 6-Dimethylamino hexanoic acid methyl ester

HRID 2090130

반응식

HRID 2090130 반응식
[CH:1](O)=[O:2].CCN(C([C@@H]1C=[C:25]2[C@@H:14](CC3C4[C:21]2=[CH:22][CH:23]=[CH:24]C=4NC=3)[N:13]([CH3:27])[CH2:12]1)=O)CC.[OH2:28]>C(#N)C>[CH3:1][O:2][C:24](=[O:28])[CH2:23][CH2:22][CH2:21][CH2:25][CH2:14][N:13]([CH3:12])[CH3:27]

참가 물질

5

반응물 3

HCID 284Formic Acid2회HCID 962WaterHCID 5761(+)-Lysergic acid diethylamide

생성물 1

HCID 540390256-Dimethylamino hexanoic acid methyl ester

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

[2-Diethoxy-phosphoryloxy)-ethyl]-(5-methoxycarbonyl-pentyl)-dimethylammonium trifluoroacetate. The methyl ester (1.73 g, 10 mmol) was dissolved in dry acetonitrile (15 mL) and K2CO3 (1.38 g, 10 mmol) was added. This suspension was refluxed under nitrogen gas for 36 h. After cooling to room temperature water was added and the pH was adjusted to 2 by adding TFA. The solution was purified by rp HPLC (Supelco Discovery C18, 21.2 mm×15 cm, 5 μm, A: 5% IPA, 95% H2O, 0.1% TFA, B: 90% IPA, 10% H2O, 0.1% TFA, 0 to 15% B over 14 min, tR=11.8 min) and lyophilized to give the TFA salt of the quaternary amine as light yellow oil (1.06 g, 3.0 mmol, 30%). LC-MS (Phenomenex Gemini, C18, 5 μm, 150×3.0 mm, A: 0.1% formic acid in water, B: 0.1% formic acid in acetonitrile, 10-50% B over 10 min) tR=6.4 min (LSD signal), m/z=354.2 for [M±H]+. 1NMR (CD3OD, 400 MHz) δ=1.41-1.50 (m, 8H, 2×OCH2CH3 and CH2); 1.77 (m, 2H, CH2); 1.90 (m, 2H, CH2); 2.44 (t, 2H, CH2, 3J=7.2 Hz); 3.25 (s, 6H, N(CH3)2); 3.48 (m, 2H, CH2); 3.72 (s, 3H, COOCH3) 3.82 (m, 2H, CH2); 4.26 (dq, 4H, 2×CH2CH3, 3J(H,H)=6.8 Hz, 3J(H,P)=8.0 Hz); 4.58 (brs, 2H, CH2). 13C NMR (CD3OD, 100.5 MHz) δ=16.4 (d, 2×OCH2CH3, 3J=6.1 Hz); 23.3 (CH2); 25.3 (CH2); 26.7 (CH2); 34.4 (CH2); 52.0 (CH3); 52.2 (CH3); 62.1 (d, CH2, 2J=5.3 Hz); 64.8 (CH2); 66.1 (d, CH2, 2J=6.1 Hz); 66.7 (CH2); 175.5 (CO).

출처 및 근거

ORD 기록
ord-742f5e9d8e074f9bbb0319e421aaf101
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436138B2

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