Dimethylformamide → (R)-3-(5-(hex-1-ynyl)furan-2-carboxamido)-4-(trimethylammonio)butanoate

HRID 1958705Notes

Reaction equation

HRID 1958705 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].[C:12]([C:18]1[O:22][C:21]([C:23](ON2C(=O)CCC2=O)=[O:24])=[CH:20][CH:19]=1)#[C:13][CH2:14][CH2:15][CH2:16][CH3:17].CN(C=O)C.C(N(CC)CC)C>C(OCC)C>[C:12]([C:18]1[O:22][C:21]([C:23]([NH:11][C@@H:6]([CH2:5][N+:2]([CH3:3])([CH3:4])[CH3:1])[CH2:7][C:8]([O-:10])=[O:9])=[O:24])=[CH:20][CH:19]=1)#[C:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 121830EmeriamineHCID 86641214HCID 86641214, compound

Product 1

HCID 59294386(R)-3-(5-(hex-1-ynyl)furan-2-carboxamido)-4-(trimethylammonio)butanoateYield 40%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(R)-aminocarnitine (20 mg, 0.12 mmol) and 2,5-dioxopyrrolidin-1-yl 5-(hex-1-ynyl)furan-2-carboxylate (68 mg, 0.23 mmol) were dissolved into DMF (1 mL). Triethylamine (50 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 powder was purified by silica gel chromatography (elution 10% MeOH/CH2Cl2 to 80% MeOH/CH2Cl2) to give the title compound as a white powder (16 mg, 40%). 1H NMR (400 MHz, D2O) δ 7.02 (d, 1H, J=3.7 Hz), 6.53 (d, 1H, J=3.6 Hz), 4.90-4.80 (m, 1H), 3.63-3.58 (m, 1H), 3.47-3.42 (m, 1H), 3.06 (s, 9H), 2.45-2.42 (m, 2H), 2.35 (t, 2H, J=6.9 Hz), 1.47-1.41 (m, 2H), 1.35-1.29 (m, 2H), 0.78 (t, 3H, J=7.3 Hz); MS ESI 335.2 [M+H]+, calcd for [C18H26N2O4+H]+ 335.19.

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-49c0cae1c7494dffa6b95ed01501d30f
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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