Hexane → 4,6-Dibromo-2-(2-phenyl-propionylamino)-benzoic acid methyl ester

HRID 735225Notes

Reaction equation

HRID 735225 reaction equation
[C:1]1([CH:7]([CH3:11])[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=S(Cl)Cl.[CH3:16][O:17][C:18](=[O:28])[C:19]1[C:24]([Br:25])=[CH:23][C:22]([Br:26])=[CH:21][C:20]=1[NH2:27].CCCCCC>CCOC(C)=O>[CH3:16][O:17][C:18](=[O:28])[C:19]1[C:24]([Br:25])=[CH:23][C:22]([Br:26])=[CH:21][C:20]=1[NH:27][C:8](=[O:10])[CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:11]

Participants

6

Reactant 4

HCID 8058HexaneHCID 102962-Phenylpropionic acidHCID 24386Thionyl ChlorideHCID 68817243Methyl 2-amino-4,6-dibromobenzoate

Product 1

HCID 688165794,6-Dibromo-2-(2-phenyl-propionylamino)-benzoic acid methyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the intermediate 1, using a 2-phenyl-propionic acid (2.00 g, 13.3 mmol), SOCl2 (3.47 mL, 40.0 mmol), and 2-amino-4,6-dibromo-benzoic acid methyl ester (2.74 g, 8.88 mmol). After normal workup, the pure objective compound (3.60 g, 92%) was obtained as white solid by a flash column chromatography (n-hexane:EtOAc=20:1): 1H NMR (200 MHz, CDCl3) δ 1.60 (d, J=7.3 Hz, 3H, CH3), 3.65-3.75 (m, 4H, CO2CH3 & CH) 7.24-7.44 (m, 5H, ArH), 7.48 (d, J=2.0 Hz, 1H, ArH), 8.55 (d, J=2.0 Hz, 1H, ArH), 8.68 (br s, 1H, NH).

Sources & evidence

ORD record
ord-8138e5c83a4943f4938c8a0b8169bf51
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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