Chloride → HCID 22986175, compound

Starting material (18(e)) was prepared as follows. A suspension of isophthalic acid monomethyl ester (18(a)), (2.65 g, 14.7 mmol) in CH2Cl2 (100 mL) and DMF (10 drops) was treated with oxallyl chloride (2.6 ml, 29.8 mmol) at 0° under argon. The reaction mixture was allowed to warm to room temperature over 18 h. The resulting solution was concentrated and azeotroped with toluene to give a crystalline yellow solid. This was then redissolved in CH2Cl2 (100 mL) and added dropwise to a stirred solution of 3,4-dichlorobenzylamine (2.6 g. 14.7 mmol) and Et3N (5 mL, 35.9 mmol) in CH2Cl2 (100 mL) at 0° under argon. The resulting solution was allowed to warm to room temperature over 4 hours. washed with 1N HCl(50 mL), saturated NaHCO3 (aq) (50 mL), dried over MgSO4, filtered and concentrated to an orange oil. This was then purified by flash chromatography on 9385 SiO2 eluting on a gradient of 25-50% EtOAc/i-Hexane to yield 3-(3,4-dichlorobenzyl-carbamoyl)-benzoic acid methyl ester (18(b)) as a pale yellow oil: 3.99 g (80%).

1. customwas prepared
2. concentrationThe resulting solution was concentrated
3. customazeotroped with toluene
4. customto give a crystalline yellow solid
5. temperatureto warm to room temperature over 4 hours
6. washwashed with 1N HCl(50 mL), saturated NaHCO3 (aq) (50 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated to an orange oil
10. customThis was then purified by flash chromatography on 9385 SiO2 eluting on a gradient of 25-50% EtOAc/i-Hexane

ORD record

ord-10017e28b3d54e229ab8a54000a2181c

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06541491B1