Dimethylformamide → Methyl 4-hydroxy-3-iodobenzoate

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Isopropyl iodide	HCID 6362	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1,1-dimethylethyl (4R)-4-({[(1,1-dimethylethyl)oxy]carbonyl)amino)-5-[4-(1-methyl-2-{[methyl(methyloxy)amino]carbonyl}-1H-imidazol-4-yl)phenyl]pentanoate	HCID 86604766	—
Product	Methyl 4-hydroxy-3-iodobenzoate	HCID 11346465	20%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a solution of compound 1 (200 mg, 1.077 mmol) and 2-iodopropane, (322 uL, 3.23 mmol) in DMF (10 mL) was added DIEA (750 uL, 4.31 mmol). The reaction mixture was heated to 80° C. and stirred overnight. The reaction was monitored by LC/MS. After the reaction was done it was cooled to room temperature. The reaction mixture was quenched with HCl (0.5 N, 30 mL) and extracted with ethyl acetate (50 mL×3). The organic layer was dried over sodium sulfate and concentrated and dried under high vacuum. The resulting residue was purified by reverse phase chromatography using a mixture of acetonitrile and water to give compound 2 (50 mg, 20%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07795448B2
Source dataset	uspto-grants-2010_09
ORD ID	ord-e2e4cc66bc86493ba08e952ba9ad5ca2
Source note	uspto-grants-2010_09