2,3,4-Trifluorophenyl isocyanate → (R)-3-Carboxy-N,N,N-trimethyl-2-(3-(2,3,4-trifluorophenyl)ureido)-propan-1-aminium acetate

HRID 1958714Notes

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.[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[C:16]([F:23])[C:15]=1[F:24]>>[C:10]([O-:12])(=[O:11])[CH3:9].[C:10]([CH2:9][C@@H:2]([NH:1][C:21]([NH:20][C:17]1[CH:18]=[CH:19][C:14]([F:13])=[C:15]([F:24])[C:16]=1[F:23])=[O:22])[CH2:4][N+:5]([CH3:8])([CH3:7])[CH3:6])([OH:11])=[O:12]

Participants

Reactant 2

HCID 27333932,3,4-Trifluorophenyl isocyanate

HCID 10397311Aminocamitine

Product 1

HCID 68746205(R)-3-Carboxy-N,N,N-trimethyl-2-(3-(2,3,4-trifluorophenyl)ureido)-propan-1-aminium acetate

Procedure

According to the method described in example S11, aminocarnitine (41 mg) was reacted with 1,2,3-trifluoro-4-isocyanatobenzene to yield the title compound as a white solid (2.3 mg). 1H NMR (400 MHz, CD3OD): δ=7.70-7.60 (m, 1H), 7.10-7.00 (m, 1H), 4.61 (br s, 1H), 3.80-45 (m, 2H), 3.22 (s, 9H), 2.40-2.60 (m, 2H), 1.97 (s, 3H); MS ESI [M+H]+, calcd for [C14H18F3N3O3+H]+ 334.3 found m/z 334.1 (100)

Sources & evidence

ORD record: ord-9c1abfb4e86443f48186c824a050ad19
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410150B2

Reaction notes

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