1-Benzyl-3-isocyanatobenzene → (r)-3-(3-(3-Benzylphenyl)ureido)-4-(trimethylammonio)butanoate

HRID 1958748Notes

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

Participants

Reactant 2

HCID 41227751-Benzyl-3-isocyanatobenzene

HCID 10397311Aminocamitine

Product 1

HCID 59294391(r)-3-(3-(3-Benzylphenyl)ureido)-4-(trimethylammonio)butanoateYield 93.4%

Procedure

According to the method described in example S11, aminocarnitine (1.28 HBr salt, 68 mg, 0.31 mmol) was reacted with 1-benzyl-3-isocyanatobenzene (132 mg, 0.63 mmol) to yield the title compound as a white solid (107 mg, 92%). NMR (400 MHz, CD3OD) δ=ppm 7.11-7.29 (m, 8H), 6.83 (d, J=7.33 Hz, 1H), 4.58 (br. s, 1 H), 3.89 (s, 2 H), 3.71 (dd, J=13.64, 9.35 Hz, 1 H), 3.50 (d, J=13.39 Hz, 1 H), 3.17 (s, 9 H), 2.40-2.58 (m, 2 H). MS ESI [M+H]+, calcd for [C21H27N3O3+H]+ 370.46 found m/z 370.2 (100).

Sources & evidence

ORD record: ord-e2c3e44713354cfaaae51fdfc89a7959
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410150B2

Reaction notes

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