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

HRID 1958709Notes

Reaction equation

HRID 1958709 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]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:26][CH:25]=1)=[C:22]=[O:23]>CO>[O: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)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 121830EmeriamineHCID 27348964-Phenoxyphenyl isocyanate

Product 1

HCID 25065919(R)-3-(3-(4-phenoxyphenyl)ureido)-4-(trimethylammonio)butanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-aminocarnitine (27 mg, 0.17 mmol) and diisopropylethylamine (88 uL, 0.51 mmol) in MeOH (2 mL) was added 1-isocyanato-4-phenoxybenzene (71 mg, 0.34 mmol) and the reaction stirred for 18 h. The MeOH was removed in vacuo and the residue stirred with 1:1 ether/EtOAc. Impurities were dissolved in the ether/EtOAc and discarded and the remaining material was 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 (10 mg, 16%). 1H NMR (400 MHz, CD3OD) δ 7.37-7.30 (m, 4H), 7.07 (t, 1H, J=7.2 Hz), 6.95-6.92 (m, 4H), 4.73-4.71 (m, 1H), 3.80-3.54 (m, 2H), 3.26 (s, 9H), 2.81-2.68 (m, 2H); MS ESI 372.2 [M+H]+, calcd for [C20H25N3O4+H]+ 372.43.

Workup

  1. customThe MeOH was removed in vacuo
  2. stirringthe residue stirred with 1:1 ether/EtOAc
  3. dissolutionImpurities were dissolved in the ether/EtOAc
  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 (10 mg, 16%)

Sources & evidence

ORD record
ord-27aedca7b1ca4390b4e08354b57a0f56
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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