Diisopropylethylamine → HCID 25065917, compound

HRID 1958711Notes

Reaction equation

HRID 1958711 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.[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]=[C:36]=[O:37])=[CH:31][CH:30]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CO>[CH2:21]([O:28][C:29]1[CH:30]=[CH:31][C:32]([NH:35][C:36](=[O:37])[NH:11][C@@H:6]([CH2:5][N+:2]([CH3:3])([CH3:4])[CH3:1])[CH2:7][C:8]([O-:10])=[O:9])=[CH:33][CH:34]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 121830EmeriamineHCID 27333844-(Heptyloxy)phenyl isocyanate

Product 1

HCID 25065917HCID 25065917, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-aminocarnitine (16 mg, 0.10 mmol) and diisopropylethylamine (52 uL, 0.30 mmol) in MeOH (2 mL) was added 1-(heptyloxy)-4-isocyanatobenzene (46 uL, 0.20 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, 23%). 1H NMR (400 MHz, CD3OD) δ 7.24 (d, 2H, J=9.2 Hz), 6.84 (d, 2H, J=8.8 Hz), 4.71-4.69 (m, 1H), 3.93 (t, 2H, J=6.4 Hz), 3.77-3.53 (m, 2H), 3.25 (s, 9H), 2.74-2.70 (m, 2H), 1.77-1.72 (m, 2H), 1.49-1.34 (m, 8H), 0.92 (t, 3H, J=6.8 Hz); MS ESI 394.3 [M+H]+, calcd for [C21H35N3O4+H]+ 394.52.

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, 23%)

Sources & evidence

ORD record
ord-f1bc3c59fab8438c91f05d9037c4c754
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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