Hexane → 4,6-Dichloro-2-[2-(4-methoxy-phenyl)-propionylamino]-benzoic acid methyl ester

HRID 735227Notes

Reaction equation

HRID 735227 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([OH:12])=O)=[CH:5][CH:4]=1.O=S(Cl)Cl.[CH3:18][O:19][C:20](=[O:30])[C:21]1[C:26]([Cl:27])=[CH:25][C:24]([Cl:28])=[CH:23][C:22]=1[NH2:29].CCCCCC>CCOC(C)=O>[CH3:18][O:19][C:20](=[O:30])[C:21]1[C:26]([Cl:27])=[CH:25][C:24]([Cl:28])=[CH:23][C:22]=1[NH:29][C:10](=[O:12])[CH:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[CH3:13]

Participants

6

Reactant 4

HCID 8058HexaneHCID 24386Thionyl ChlorideHCID 257576p-Methoxyphenylpropionic acidHCID 12363232Methyl 2-amino-4,6-dichlorobenzoate

Product 1

HCID 688184034,6-Dichloro-2-[2-(4-methoxy-phenyl)-propionylamino]-benzoic acid methyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the intermediate 1, using a 2-(4-methoxy-phenyl)-propionic acid (1.45 g, 8.0 mmol), SOCl2 (2.09 mL, 24.0 mmol), and 2-amino-4,6-dichloro-benzoic acid methyl ester (1.54 g, 7.0 mmol). After normal workup, the pure objective compound (2.27 g, 85%) was obtained as pale yellow syrup by a flash column chromatography (n-hexane:EtOAc=10:1): 1H NMR (200 MHz, CDCl3) δ 1.56 (d, J=7.0 Hz, 3H, CH3), 3.77 (s, 3H, CO2CH3), 3.81 (s, 3H, OCH3), 3.84-3.95 (m, 1H, CH), 6.83-6.97 (m, 2H, ArH), 7.12 (d, J=2.0 Hz, 1H, ArH), 7.21-7.27 (m, 2H, ArH), 8.41 (d, J=2.0 Hz, 1H, ArH), 8.98 (s, 1H, NH); HRMS(EI) calcd. for C18H17O4NCl2 m/e 381.0536 [M+], found 381.0539.

Sources & evidence

ORD record
ord-596fe8235a8a4b3bbad0c286b42e56c0
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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