Dimethylformamide → (R)-3-(4-propoxybenzamido)-4-(trimethylammonio)butanoate

HRID 1958703노트

반응식

HRID 1958703 반응식
[CH3:1][N+:2]([CH2:5][C@H:6]([NH2:11])[CH2:7][C:8]([O-:10])=[O:9])([CH3:4])[CH3:3].[CH2:12]([O:15][C:16]1[CH:31]=[CH:30][C:19]([C:20](ON2C(=O)CCC2=O)=[O:21])=[CH:18][CH:17]=1)[CH2:13][CH3:14].CN(C=O)C.C(N(C(C)C)CC)(C)C>C(OCC)C>[CH2:12]([O:15][C:16]1[CH:31]=[CH:30][C:19]([C:20]([NH:11][C@@H:6]([CH2:5][N+:2]([CH3:3])([CH3:4])[CH3:1])[CH2:7][C:8]([O-:10])=[O:9])=[O:21])=[CH:18][CH:17]=1)[CH2:13][CH3:14]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 121830EmeriamineHCID 866412122,5-Dioxopyrrolidin-1-yl 4-propoxybenzoate

생성물 1

HCID 25065699(R)-3-(4-propoxybenzamido)-4-(trimethylammonio)butanoate수율 21%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

(R)-aminocarnitine (20 mg, 0.12 mmol) and 2,5-dioxopyrrolidin-1-yl 4-propoxybenzoate (42 mg, 0.15 mmol) were dissolved into DMF (0.5 mL). Diisopropylethylamine (63 μL, 0.36 mmol) was added and the solution was stirred at room temperature for 18 h. Diethyl ether (20 mL) was added and a white precipitate was collected. The white solid was triturated with 1:1 acetone/ether and dried to give the title compound as a white powder (8.1 mg, 21%). 1H NMR (300 MHz, CD3OD) δ 7.89-7.78 (m, 2H), 7.01 (d, 2H, J=7.8 Hz), 4.75-4.63 (m, 1H), 4.02 (t, 2H, J=7.2 Hz), 3.75-3.51 (m, 2H), 3.21 (s, 9H), 2.82-2.71 (m, 2H), 1.85-1.75 (m, 2H), 1.05 (t, 3H, J=7.0 Hz); MS ESI 323.1 [M+H]+, calcd for [C17H26N2O4+H]+ 323.19.

후처리

  1. customa white precipitate was collected
  2. customThe white solid was triturated with 1:1 acetone/ether
  3. customdried

출처 및 근거

ORD 기록
ord-4ef705310fd2495292be8cb121fc174f
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410150B2

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