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

HRID 1958703ノート

反応式

HRID 1958703 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

(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.

後処理

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

出典と根拠

ORDレコード
ord-4ef705310fd2495292be8cb121fc174f
出典データセット
uspto-grants-2013_04
特許番号
US08410150B2

反応ノート

読み込み中…