Diisopropylethylamine → (R)-3-(3-(2-chloro-4-(trifluoromethyl)phenyl)ureido)-4-(trimethylammonio)-butanoate

HRID 1958707Notes

Reaction equation

HRID 1958707 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.[Cl:21][C:22]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:23]=1[N:32]=[C:33]=[O:34]>CO>[Cl:21][C:22]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:23]=1[NH:32][C:33](=[O:34])[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 51025332-Chloro-4-(trifluoromethyl)phenyl isocyanate

Product 1

HCID 25065913(R)-3-(3-(2-chloro-4-(trifluoromethyl)phenyl)ureido)-4-(trimethylammonio)-butanoateYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-aminocarnitine (35 mg, 0.22 mmol) and diisopropylethylamine (0.11 mL, 0.65 mmol) in MeOH (2 mL) was added 2-chloro-1-isocyanato-4-(trifluoromethyl)benzene (67 uL, 0.44 mmol) and the reaction stirred at room temperature overnight. The MeOH was removed in vacuo and the residue titurated several times with 1:1 ether/EtOAc, the resulting solid was filtered and dried to give the title compound as a white powder (15 mg, 18%). NMR (300 MHz, CD3OD) δ 8.37 (m, 1H), 7.68 (m, 1H), 7.53 (m, 1H), 4.29 (m, 1H), 3.78-3.48 (m, 2H), 3.25 (s, 9H), 2.70-2.49 (m, 2H); MS ESI 382.1 [M+H]+, calcd for [C15H19ClF3N3O3+H]+ 382.78.

Workup

  1. customThe MeOH was removed in vacuo
  2. filtrationthe resulting solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-adec79a6b6274e809eb4180f248231a6
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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