1,2-Dichloroethane → Methyl-2-[4-({(2s)-2-(acetylamino)-3-[4-(1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]propanoyl}amino)butoxy]-6-hydroxybenzoate

Participants

Role	Name	HCID	Charge
Reactant	1,2-Dichloroethane	HCID 11	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methyl 2-(4-aminobutoxy)-6-hydroxybenzoate hydrochloride	HCID 69597617	—
Reactant	(2s)-2-[(Tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]propanoic acid	HCID 69597956	—
Solvent	Dichloromethane	HCID 6344	—
Product	Methyl-2-[4-({(2s)-2-(acetylamino)-3-[4-(1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]propanoyl}amino)butoxy]-6-hydroxybenzoate	HCID 69598091	53.6%

Reaction Conditions

Temperature	40 °C

Reaction Steps

21-A (Bioorg. & Medchem. Lett. (2003), 13, 3129–3132) (8 mg, 0.029 mmol) was added to a DCM (0.1 M) solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]propanoic acid (12 mg, 0.027 mmol), EDC (5 mg, 0.027 mmol), HOBt (3.6 mg, 0.027 mmol) and DIEA (10 μL, 0.029 mmol). The reaction was stirred at 40° C. for 4 h and then concentrated. The crude was purified by reverse phase HPLC to afford 21-B (8.1 mg, 44%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07141596B2
Source dataset	uspto-grants-2006_11
ORD ID	ord-218d758e599b4be6b5f65cd837b09be8
Source note	uspto-grants-2006_11