Sodium 2-ethylhexanoate → (2R,3R,4S,5R,6E)-7-cyclopentyl-N-[(3S)-1,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]-3,4,5-trihydroxy-2-methoxyhept-6-enamide

Participants

Role	Name	HCID	Charge
Reactant	Sodium 2-ethylhexanoate	HCID 23672331	—
Reactant	(3R,4R,5S)-5-[(1R,2E)-3-cyclopentyl-1-hydroxyprop-2-en-1-yl]-4-hydroxy-3-methoxydihydrofuran-2(3H)-one	HCID 57463784	—
Reactant	(3S)-3-amino-1,5-dimethyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one hydrochloride	HCID 67329118	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(2R,3R,4S,5R,6E)-7-cyclopentyl-N-[(3S)-1,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]-3,4,5-trihydroxy-2-methoxyhept-6-enamide	HCID 57617735	—

Reaction Steps

208 mg of 32 (852 μmol), 198 mg of 18 (0.712 mmol) and 473 mg of sodium 2-ethylhexanoate (2.848 mmol) in 5 mL of THF are successively introduced into a 25 mL round-bottomed flask, with stirring and under an argon atmosphere. The stirring is maintained at RT for 2 days. The mixture is concentrated under vacuum. The crude product is chromatographed on a silica cartridge [50 g, eluent AcOEt/AcOEt-isopropanol (50/50), in an AcOEt-isopropanol (50/50) gradient: 0 to 30%]). 172 mg of expected product Ex15 are recovered.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07994161B2
Source dataset	uspto-grants-2011_08
ORD ID	ord-b8afad34d2cc4d1fb9b01845eb942a87
Source note	uspto-grants-2011_08