Dimethylformamide → (R)-3-(4-(3-methylfuran-2-carboxamido)benzamido)-4-(trimethylammonio)-butanoate

HRID 1958706Notes

Reaction equation

HRID 1958706 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].[CH3:12][C:13]1[CH:17]=[CH:16][O:15][C:14]=1[C:18]([NH:20][C:21]1[CH:36]=[CH:35][C:24]([C:25](ON2C(=O)CCC2=O)=[O:26])=[CH:23][CH:22]=1)=[O:19].CN(C=O)C.C(N(CC)CC)C>C(OCC)C>[CH3:12][C:13]1[CH:17]=[CH:16][O:15][C:14]=1[C:18]([NH:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([NH:11][C@@H:6]([CH2:5][N+:2]([CH3:3])([CH3:4])[CH3:1])[CH2:7][C:8]([O-:10])=[O:9])=[O:26])=[CH:23][CH:22]=1)=[O:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 121830EmeriamineHCID 866412152,5-Dioxopyrrolidin-1-yl 4-(3-methylfuran-2-carboxamido)benzoate

Product 1

HCID 59294354(R)-3-(4-(3-methylfuran-2-carboxamido)benzamido)-4-(trimethylammonio)-butanoateYield 43%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(R)-aminocarnitine (20 mg, 0.12 mmol) and 2,5-dioxopyrrolidin-1-yl 4-(3-methylfuran-2-carboxamido)benzoate (82 mg, 0.24 mmol) were dissolved into DMF (1 mL). Triethylamine (50 μL, 0.36 mmol) was added and the solution was stirred at room temperature for 48 h. Diethyl ether (20 mL) was added and a white precipitate was collected. The powder was purified by silica gel chromatography (elution 10% MeOH/CH2Cl2 to 80% MeOH/CH2Cl2) to give the title compound as a white solid (20 mg, 43%). 1H NMR (400 MHz, D2O) δ 7.62 (d, 1H, J=1.4 Hz), 7.32-7.30 (m, 1H), 7.27-7.16 (m, 3H), 6.55 (d, 1H, J=1.8 Hz), 4.90-4.80 (m, 1H), 3.63-3.42 (m, 2H), 3.13 (s, 9H), 2.48-2.45 (m, 2H), 2.10 (s, 3H); MS ESI 388.2 [M+H]+, calcd for [C20H25N3O5+H]+ 388.18.

Workup

  1. customa white precipitate was collected
  2. customThe powder was purified by silica gel chromatography (elution 10% MeOH/CH2Cl2 to 80% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-00b1304a8e8d445c88a658ea7aeba7c0
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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