Diisopropylethylamine → (R)-3-(3-(4-methyl-2-phenylthiazol-5-yl)ureido)-4-(trimethylammonio)-butanoate

HRID 1958710Notes

Reaction equation

HRID 1958710 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[S:28][C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:26][C:25]=1[CH3:35])=[C:22]=[O:23]>CO>[CH3:35][C:25]1[N:26]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[S:28][C:24]=1[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]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 121830EmeriamineHCID 49612625-Isocyanato-4-methyl-2-phenyl-1,3-thiazole

Product 1

HCID 25065921(R)-3-(3-(4-methyl-2-phenylthiazol-5-yl)ureido)-4-(trimethylammonio)-butanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-aminocarnitine (21 mg, 0.13 mmol) and diisopropylethylamine (68 uL, 0.39 mmol) in MeOH (2 mL) was added 5-isocyanato-4-methyl-2-phenylthiazole (57 mg, 0.26 mmol) and the reaction stirred for 18 hrs. 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 yellow powder (6 mg, 12%). 1H NMR (400 MHz, CD3OD) δ 7.85-7.82 (m, 2H), 7.47-7.41 (m, 3H), 4.73-4.71 (m, 1H), 3.82-3.57 (m, 2H), 3.26 (s, 9H), 2.79-2.75 (m, 2H), 2.37 (s, 3H); MS ESI 377.1 [M+H]+, calcd for [C18H24N4O3S+H]+ 377.47.

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 yellow powder (6 mg, 12%)

Sources & evidence

ORD record
ord-a11d2a9a9e1849178f67773dfb4c6eee
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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