Hexane → 2-[2-(4-Bromo-phenyl)-propionylamino]-4,6-dichlorobenzoic acid methyl ester

HRID 735229Notes

Reaction equation

HRID 735229 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.O=S(Cl)Cl.[CH3:17][O:18][C:19](=[O:29])[C:20]1[C:25]([Cl:26])=[CH:24][C:23]([Cl:27])=[CH:22][C:21]=1[NH2:28].CCCCCC>CCOC(C)=O>[CH3:17][O:18][C:19](=[O:29])[C:20]1[C:25]([Cl:26])=[CH:24][C:23]([Cl:27])=[CH:22][C:21]=1[NH:28][C:9](=[O:11])[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH3:12]

Participants

6

Reactant 4

HCID 8058HexaneHCID 24386Thionyl ChlorideHCID 5214412-(4-Bromophenyl)propanoic acidHCID 12363232Methyl 2-amino-4,6-dichlorobenzoate

Product 1

HCID 688165642-[2-(4-Bromo-phenyl)-propionylamino]-4,6-dichlorobenzoic acid methyl esterYield 55%

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-bromo-phenyl)-propionic acid (11.7 g, 48.3 mmol), SOCl2 (35.0 mL, 480 mmol), and 2-amino-4,6-dichloro-benzoic acid methyl ester (10.1 g, 45.9 mmol). After normal workup, the pure objective compound (9.31 g, 55%) was obtained as white solid by a flash column chromatography (n-hexane:EtOAc=10:1): 1H NMR (200 MHz, CDCl3) δ 1.58 (d, J=7.1 Hz, 3H, CH3), 3.75 (q, J=7.1 Hz, 1H, CH), 3.81 (s, 3H, CO2CH3), 7.15 (d, J=2.0 Hz, 1H, ArH), 7.20-7.53 (m, 4H, ArH), 8.41 (d, J=1.7 Hz, 1H, ArH), 9.16 (br s, 1H, NH).

Sources & evidence

ORD record
ord-84937debf36c402fba3207b121746767
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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