4-Biphenylyl isocyanate → (R)-2-(3-Biphenyl-4-ylureido)-3-carboxy-N,N,N-trimethylpropan-1-aminium acetate

HRID 1958716Notes

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]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)=[C:14]=[O:15]>>[C:10]([O-:12])(=[O:11])[CH3:9].[C:19]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:18]=[CH:17][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:21][CH:20]=1

Participants

Reactant 2

HCID 36123194-Biphenylyl isocyanate

HCID 10397311Aminocamitine

Product 1

HCID 68743216(R)-2-(3-Biphenyl-4-ylureido)-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-isocyanatobiphenyl to yield the title compound as a white solid (25.7 mg). 1H NMR (400 MHz, CD3OD): δ=7.58-7.45 (m, 6H), 7.39 (t, J=7.60 Hz, 2H), 7.28 (t, J=7.20, 1H), 4.66 (br s, 1H), 3.74 (dd, J=9.20 Hz, 13.20 Hz, 1H), 3.54 (d, 13.6 Hz, 1H), 3.23 (s, 9H), 2.65-2.55 (m, 2H), 1.98 (s, 3H). MS ESI [M+H]+, calcd for [C20H25N3O3+H]+: 356.4 found m/z 356.2 (100).

Sources & evidence

ORD record: ord-ae52723c10474e18bdff90c1a873fc1e
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410150B2

Reaction notes

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