Diisopropylethylamine → (R)-3-(3-(4-octylphenyl)ureido)-4-(trimethylammonio)butanoate

HRID 1958708Notes

Reaction equation

HRID 1958708 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(N(C(C)C)CC)(C)C.[N:21]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:26][CH:25]=1)=[C:22]=[O:23]>CO>[CH2:30]([C:27]1[CH:26]=[CH:25][C:24]([NH:21][C:22](=[O:23])[NH:11][C@@H:6]([CH2:5][N+:2]([CH3:3])([CH3:4])[CH3:1])[CH2:7][C:8]([O-:10])=[O:9])=[CH:29][CH:28]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 121830EmeriamineHCID 37026561-Isocyanato-4-octylbenzene

Product 1

HCID 25065911(R)-3-(3-(4-octylphenyl)ureido)-4-(trimethylammonio)butanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-aminocarnitine (22 mg, 0.14 mmol) and diisopropylethylamine (71 uL, 0.41 mmol) in MeOH (2 mL) was added 1-isocyanato-4-octylbenzene (63 uL, 0.27 mmol) and the reaction stirred for 18 h. The MeOH was removed in vacuo and the residue stirred with 1:1 ether/EtOAc. Impurities dissolved into the ether/EtOAc which were discarded and the remaining material taken up into 90:10 CH2Cl2/MeOH and then loaded onto a short SiOH plug. The title compound was eluted by increasing MeOH content in 10% steps to 60%. The compound was then taken up into 90:10 CH2Cl2/MeOH and filtered through a plug of celite which gave after drying the title compound as a white powder (9 mg, 17%). 1H NMR (400 MHz, CD3OD) δ 7.27 (d, 2H, J=8.4 Hz), 7.09 (d, 2H, J=8.4 Hz), 4.73-4.71 (m, 1H), 3.78-3.53 (m, 2H), 3.25 (s, 9H), 2.75-2.72 (m, 2H), 2.55 (t, 2H, J=8.0 Hz), 1.60-1.29 (m, 12H), 0.90 (t, 3H, J=6.8 Hz); MS ESI 392.3 [M+H]+, calcd for [C22H37N3O3+H]+ 392.55.

Workup

  1. customThe MeOH was removed in vacuo
  2. stirringthe residue stirred with 1:1 ether/EtOAc
  3. dissolutionImpurities dissolved into the ether/EtOAc which
  4. washThe title compound was eluted
  5. temperatureby increasing MeOH content in 10% steps to 60%
  6. filtrationfiltered through a plug of celite which
  7. customgave
  8. dry with materialafter drying the title compound as a white powder (9 mg, 17%)

Sources & evidence

ORD record
ord-aeaefab6b7eb4f66821f06e1b7567be9
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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