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Dimethylformamide → (R)-3-(5-(phenylethynyl)furan-2-carboxamido)-4-(trimethylammonio)-butanoate

HRID 1958704
Notes
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Reaction equation

HRID 1958704 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]1([C:18]#[C:19][C:20]2[O:24][C:23]([C:25](ON3C(=O)CCC3=O)=[O:26])=[CH:22][CH:21]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CN(C=O)C.C(N(CC)CC)C>C(OCC)C>[C:12]1([C:18]#[C:19][C:20]2[O:24][C:23]([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:22][CH:21]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 121830EmeriamineHCID 574408102,5-Dioxopyrrolidin-1-yl 5-(phenylethynyl)furan-2-carboxylate

Product 1

HCID 25064262(R)-3-(5-(phenylethynyl)furan-2-carboxamido)-4-(trimethylammonio)-butanoateYield 28.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(R)-aminocarnitine (16 mg, 0.1 mmol) and 2,5-dioxopyrrolidin-1-yl 5-(phenylethynyl)furan-2-carboxylate (60 mg, 0.19 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 100% MeOH) to give the title compound as a white powder (10 mg, 24%). 1H NMR (400 MHz, D2O) δ 7.35-7.33 (m, 2H), 7.25-7.16 (m, 3H), 7.02 (d, 1H, J=3.7 Hz), 6.58 (d, 1H, J=3.6 Hz), 4.90-4.80 (m, 1H), 3.63-3.55 (m, 1H), 3.47-3.42 (m, 1H), 3.04 (s, 9H), 2.51-2.41 (m, 2H); MS ESI 355.1 [M+H]+, calcd for [C20H22N2O4+H]+ 355.16.

Workup

  1. customa white precipitate was collected
  2. customThe powder was purified by silica gel chromatography (elution 10% MeOH/CH2Cl2 to 100% MeOH)

Sources & evidence

ORD record
ord-17f34410deaf4abf84b27a5b6361fe33
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08410150B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes