4-Isocyanatobenzophenone → (R)-2-(3-(4-Benzoylphenyl)ureido)-3-carboxy-N,N,N-trimethylpropan-1-aminium acetate

HRID 1958715Notes

Reaction equation

HRID 1958715 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.[N:13]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])=[CH:18][CH:17]=1)=[C:14]=[O:15]>>[C:10]([O-:12])(=[O:11])[CH3:9].[C:22]([C:19]1[CH:20]=[CH:21][C:16]([NH:13][C:14](=[O:15])[NH:1][C@H:2]([CH2:9][C:10]([OH:11])=[O:12])[CH2:4][N+:5]([CH3:8])([CH3:7])[CH3:6])=[CH:17][CH:18]=1)(=[O:23])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 3010774-IsocyanatobenzophenoneHCID 10397311Aminocamitine

Product 1

HCID 68745797(R)-2-(3-(4-Benzoylphenyl)ureido)-3-carboxy-N,N,N-trimethylpropan-1-aminium acetate

Procedure

According to the method described in example S11, aminocarnitine (40 mg) was reacted with (4-isocyanatophenyl)(phenyl)methanone to yield the title compound as a white solid (13.4 mg). 1H NMR (400 MHz, CD3OD): δ=7.76-7.68 (m, 4H), 7.66-7.55 (m, 3H), 7.55-7.48 (m, 2H), 4.66 (brs, 1H), 3.78 (dd, J=9.20 Hz, 13.60 Hz, 1H), 3.60-3.50 (m, 1H), 3.24 (s, 9H), 2.65-2.50 (m, 2H), 1.98 (s, 3H); MS ESI [M+H]+, calcd for [C21H26N3O4+H]+ 384.4 found m/z 384.2 (100)

Sources & evidence

ORD record
ord-c5011fd977774cbebf458a65619fe873
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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