Dimethylcarbamoyl Chloride → (S)-3-Amino-2-oxo-6-phenoxy-3,4-dihydroquinolin-1(2H)-yl dimethylcarbamate
Reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].Cl.[NH2:8][C@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=2)[N:11]([OH:26])[C:10]1=[O:27]>N1C=CC=CC=1>[NH2:8][C@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=2)[N:11]([O:26][C:3](=[O:4])[N:2]([CH3:6])[CH3:1])[C:10]1=[O:27]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Dimethylcarbamyl chloride (37 μL, 0.39 mmol) was added to a solution of (3S)-3-amino-1-hydroxy-6-phenoxy-3,4-dihydroquinolin-2(1H)-one, hydrochloride salt (93, Example 71) (100 mg, 0.33 mmol) in pyridine (2 mL). The reaction mixture was maintained at RT for 1.5 h, then concentrated in vacuo; the resulting residue was diluted with EtOAc (20 mL) and water (10 mL). The separated organic phase was washed with water (10 mL), dried over Mg2SO4, filtered, and concentrated in vacuo to provide the title compound as an oil (72 mg, 65%). LCMS m/z 253.0 [(M-dimethyl carbamic acid)+1]. 1H NMR (400 MHz, CD3OD) δ 2.94-3.02 (m, 1H), 3.02 (br s, 3H), 3.08 (dd, half of ABX pattern, J=15.5, 6.4 Hz, 1H), 3.17 (br s, 3H), 3.78 (dd, J=13.3, 6.3 Hz, 1H), 6.90-7.00 (m, 5H), 7.11 (ddt, J=7.7, 7.1, 1.1 Hz, 1H), 7.32-7.37 (m, 2H).