Water → 1-(3-Acetoxy-4-methoxy-benzoylamino)-Cycloheptanecarboxylic Acid Methyl Ester

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Benzoic acid, 3-(acetyloxy)-4-methoxy-	HCID 151620	—
Reactant	O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733286	—
Reactant	Methyl 1-aminocycloheptane-1-carboxylate hydrochloride	HCID 42614177	—
Solvent	Dimethylformamide	HCID 6228	—
Product	1-(3-Acetoxy-4-methoxy-benzoylamino)-Cycloheptanecarboxylic Acid Methyl Ester	HCID 86672564	73.5%

Reaction Steps

3-Acetoxy-4-methoxy-benzoic acid (7.10 g, 33.8 mmol) was dissolved in DMF (70 ml). The solution was cooled in an ice bath and 1-amino-cycloheptanecarboxylic acid methyl ester hydrochloride (7.72 g, 37.2 mmol), EDIA (24.4 ml, 135 mmol) and TOTU (16.6 g, 50.7 mmol) were added sequentially. Stirring was continued at room temperature for 1 h. Water was added and stirring was continued for 1 h. The solid material which formed was collected by filtration, washed with water and dried in vacuo. The obtained material was stirred with a diethyl ether/HEP mixture, filtered and dried in vacuo to yield the title compound (9.03 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09018383B2
Source dataset	uspto-grants-2015_04
ORD ID	ord-11538a1c659648199248f9fd96047d07
Source note	uspto-grants-2015_04