1-Isocyanato-3-phenoxybenzene → (r)-3-(3-(3-Phenoxyphenyl)ureido)-4-(trimethylammonio)butanoate

HRID 1958726Notes

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][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=1)=[C:14]=[O:15]>>[O:22]([C:18]1[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]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Reactant 2

HCID 34456731-Isocyanato-3-phenoxybenzene

HCID 10397311Aminocamitine

Product 1

HCID 59294389(r)-3-(3-(3-Phenoxyphenyl)ureido)-4-(trimethylammonio)butanoateYield 58%

Procedure

According to the method described in example S11, aminocamitine (1.28 HBr salt, 68 mg, 0.31 mmol) was reacted with 1-isocyanato-3-phenoxybenzene to yield the title compound as a white solid (69 mg, 58%). 1H NMR (400 MHz, CD3OD) 7.34 (t, J=7.96 Hz, 2 H), 7.17-7.23 (m, 2 H), 7.04-7.12 (m, 2 H), 6.95-7.00 (m, 1 H), 6.59 (dd, J=7.83, 2.02 Hz, 1 H), 4.57 (br. s, 1 H), 3.72 (dd, J=13.64, 9.09 Hz, 1 H), 3.46-3.56 (m, 1 H), 3.20 (s, 9 H), 2.42-2.56 (m, 2 H). MS ESI [M]+, calcd for [C20H24N3O4+H]+: 371.43 found m/z 371.7 (100).

Sources & evidence

ORD record: ord-66f706fb9e95472da50712a22680bbab
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410150B2

Reaction notes

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