Diisopropylethylamine → HCID 25065923, compound

HRID 1958712Notes

Reaction equation

HRID 1958712 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]([C:30]2[S:31][CH:32]=[CH:33][CH:34]=2)=[CH:26][CH:25]=1)=[C:22]=[O:23]>CO>[S:31]1[CH:32]=[CH:33][CH:34]=[C:30]1[C:27]1[CH:28]=[CH:29][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:25][CH:26]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 121830EmeriamineHCID 49612602-(4-isocyanatophenyl)thiophene

Product 1

HCID 25065923HCID 25065923, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-aminocarnitine (17 mg, 0.11 mmol) and diisopropylethylamine (55 uL, 0.32 mmol) in MeOH (2 mL) was added 2-(4-isocyanatophenyl)thiophene (43 mg, 0.22 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 (5 mg, 13%). 1H NMR (400 MHz, CD3OD) δ 7.53 (d, 2H, J=8.0 Hz), 7.42 (d, 2H, J=8.0 Hz), 7.29 (s, 2H), 7.05 (s, 1H), 4.65-4.63 (m, 1H), 3.77-3.53 (m, 2H), 3.23 (s, 9H), 2.58-2.48 (m, 2H); MS ESI 362.1 [M+H]+, calcd for [C18H23N3O3S+H]+ 362.46.

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 (5 mg, 13%)

Sources & evidence

ORD record
ord-510a2f19dcbd44c899497d10ee9d5d89
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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