Tetrahydrofuran → ethyl 4-[3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]anilino]-4-oxobutanoate

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Butanoic acid, 4-chloro-4-oxo-, ethyl ester	HCID 84648	—
Reactant	tert-butyl N-[4-[3-(2-amino-6-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate	HCID 145857623	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	ethyl 4-[3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]anilino]-4-oxobutanoate	HCID 145857693	—

Reaction Conditions

Temperature	50 °C

Reaction Steps

{[4-(2′-Amino-6′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (38.5 mg, 0.07 mmol, Example 25: step c) and 3-chlorocarbonyl-propionic acid ethyl ester (13 μL, 0.09 mmol) were dissolved into THF (1 mL) and heated to 50° C. for one hour. The reaction was dissolved into EtOAc and washed with brine. The combined organic layers were dried, (MgSO4) and the solvents were removed in vacuo. Purification by preparative TLC (30% EtOAc/hexanes) yielded the title compound. ESI-MS (m/z): Calcd. for C30H35N3O7S3: 646.2 (M+1); found: 645.8.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07109354B2
Source dataset	uspto-grants-2006_09
ORD ID	ord-b3c6058e890a47208ff053984d1ae172
Source note	uspto-grants-2006_09