1,2-Dichloroethane → 4-(2-Aminothiazol-4-yl)butanoyl-glycyl-2(S)-phenylsulfonamido-beta-alanine t-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	1,2-Dichloroethane	HCID 11	—
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	4-(2-Aminothiazol-4-yl)butanoic acid hydrochloride	HCID 86754465	—
Reactant	Glycyl-2(s)-phenylsulfonamido-beta-alanine t-butyl ester trifluoroacetate salt	HCID 86754466	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	4-(2-Aminothiazol-4-yl)butanoyl-glycyl-2(S)-phenylsulfonamido-beta-alanine t-butyl ester	HCID 86754469	—

Reaction Conditions

Temperature	-15 °C

Reaction Steps

Acid 1-4 (300 mg, 1.35 mmol), amine 1-7 (600 mg, 1.37 mmol), HOBT (219 mg, 1.14 mmol) and NMM (445 μL, 4.04 mmol) were combined in 13 mL DMF, cooled to −15° C., and EDC (310 mg, 1.61 mmol) was added. The reaction was warmed to RT, stirred overnight, then diluted with EtOAc, washed with water, sat. NaHCO3, and brine, dried (MgSO4), filtered and concentrated. Flash chromatography (silica, 20% MeOH/EtOAc) provided 1-8 as yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06294549B1
Source dataset	uspto-grants-2001_09
ORD ID	ord-1cff08d4a17a4910a6398a43a16fe9de
Source note	uspto-grants-2001_09