1-(3-Isocyanatophenyl)-1H-pyrrole → (r)-3-(3-(3-(1h-Pyrrol-1-yl)phenyl)ureido)-4-(trimethylammonio)butanoate

HRID 1958747Notes

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

Participants

Reactant 2

HCID 71623331-(3-Isocyanatophenyl)-1H-pyrrole

HCID 10397311Aminocamitine

Product 1

HCID 59294369(r)-3-(3-(3-(1h-Pyrrol-1-yl)phenyl)ureido)-4-(trimethylammonio)butanoateYield 63.7%

Procedure

According to the method described in example S11, aminocarnitine (1.28 HBr salt, 68 mg, 0.31 mmol) was reacted with 1-(3-isocyanatophenyl)-1H-pyrrole (116 mg, 0.63 mmol) to yield the title compound as a white solid (68 mg, 62%). 1H NMR (400 MHz, CD3OD) δ ppm=7.69 (t, J=1.89 Hz, 1 H), 7.29 (t, J=7.96 Hz, 1 H), 7.11-7.18 (m, 3 H), 6.25 (t, J=2.15 Hz, 1 H), 4.62 (br. s, 1 H), 3.76 (dd, J=13.64, 9.09 Hz, 1 H), 3.51-3.58 (m, 1 H), 3.23 (s, 9 H), 2.46-2.61 (m, 2 H). MS ESI [M+H]+, calcd for [C18H23N4O3+H]+: 344.41 found m/z 344.7 (100).

Sources & evidence

ORD record: ord-c4eaf08c4d954c71848865b0ad0bb077
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410150B2

Reaction notes

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