Benzyl (S)-(-)-tetrahydro-5-oxo-3-furanylcarbamate → (S)-Benzyl-4-(cyclopropyl(2,3-dichlorobenzyl)amino)-1-hydroxy-4-oxobutan-2-ylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	Benzyl (S)-(-)-tetrahydro-5-oxo-3-furanylcarbamate	HCID 697922	—
Reactant	Cyclopropyl-(2,3-dichloro-benzyl)-amine	HCID 834599	—
Product	(S)-Benzyl-4-(cyclopropyl(2,3-dichlorobenzyl)amino)-1-hydroxy-4-oxobutan-2-ylcarbamate	HCID 66593948	52.1%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Into a 100 mL round bottom flask fitted with a reflux condenser and a nitrogen inlet, N-(2,3-dichlorobenzyl)cyclopropanamine (30.3 g, 140.3 mmol) (Example 1A) and (S)-benzyl 5-oxotetrahydrofuran-3-ylcarbamate (22.0 g, 93.5 mmol) were added. The mixture was heated without solvent at 100° C. for 24 hours. Purification by column chromatography (5%->10% MeOH/dichloromethane) gave 22.0 g (52%) of 4A. ESI-MS:m/z 451.3 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08129538B1
Source dataset	uspto-grants-2012_03
ORD ID	ord-4b9b32a2fe7e492480c31b4bc6c1d522
Source note	uspto-grants-2012_03