Diisopropylethylamine → (R)-3-(3-(4-(Benzyloxy)phenyl)ureido)-4-(trimethylammonio)butanoate acetate

HRID 1958713Notes

Reaction equation

HRID 1958713 reaction equation
[NH2:1][C:2]([CH2:9][C:10](=[O:12])[O-:11])([CH2:4][N+:5]([CH3:8])([CH3:7])[CH3:6])O.CCN(C(C)C)C(C)C.[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]=[C:37]=[O:38])=[CH:32][CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO>[C:10]([O-:12])(=[O:11])[CH3:9].[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:38])[NH:1][C@@H:2]([CH2:4][N+:5]([CH3:8])([CH3:7])[CH3:6])[CH2:9][C:10]([OH:11])=[O:12])=[CH:32][CH:31]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2562684-(Benzyloxy)phenyl isocyanateHCID 10397311Aminocamitine

Product 1

HCID 68742644(R)-3-(3-(4-(Benzyloxy)phenyl)ureido)-4-(trimethylammonio)butanoate acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of aminocarnitine (35 mg) in anhydrous MeOH (2 mL) was treated with DIPEA (2.5 equiv) and 1-(benzyloxy)-4-isocyanatobenzene (2 equiv) at rt. The reaction was sealed and stirred at rt overnight. The reaction mixture were concentrated under reduced pressure and purified on silica gel using MeOH/DCM (0->80%) and/or 55% DCM:22% MeOH:23% AcOH. The purified material was then taken into 10% MeOH/DCM, filtered through a plug of Celite, concentrated under reduced pressure and optionally triturated with Et2O and/or hexanes to provide the title compound as a white solid (1.8 mg). 1H NMR (400 MHz, CD3OD): δ=7.42 (d, J=8.0 Hz, 2H), 7.36 (t, J=7.6, 2H), 7.30 (d, J=7.60 Hz, 1H), 7.28-7.20 (m, 2H), 6.92 (d, J=8.80 Hz, 2H), 5.04 (s, 2H), 5.59 (br s, 1H), 3.80-3.45 (m, 2H), 3.21 (s, 9H), 2.60-2.45 (br, 2H), 1.96 (s, 3H); MS ESI [M+H]+, calcd for [C21H26N3O4+H]+ 386.5 found m/z 386.2 (100).

Workup

  1. customThe reaction was sealed
  2. concentrationThe reaction mixture were concentrated under reduced pressure
  3. custompurified on silica gel
  4. filtrationfiltered through a plug of Celite
  5. concentrationconcentrated under reduced pressure
  6. customoptionally triturated with Et2O and/or hexanes

Sources & evidence

ORD record
ord-08972aa40c624f7596736343ca6cd44e
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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