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

HRID 1958703Notes

Reaction equation

HRID 1958703 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(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.

Workup

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

Sources & evidence

ORD record
ord-4ef705310fd2495292be8cb121fc174f
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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