Sodium 2-ethylhexanoate → (2R,3R,4S,5R,6E)-7-cyclopentyl-3,4,5-trihydroxy-2-methoxy-N-[(3S)-2-oxo-7-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]hept-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-7-phenyl-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one hydrochloride	HCID 67344609	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(2R,3R,4S,5R,6E)-7-cyclopentyl-3,4,5-trihydroxy-2-methoxy-N-[(3S)-2-oxo-7-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]hept-6-enamide	HCID 57463783	46.4%

Reaction Steps

100 mg of 19 (0.39 mmol), 112.6 mg of 14a (0.39 mmol) and 162 mg of sodium 2-ethylhexanoate (0.98 mmol) in 2.0 ml of THF are successively introduced into a Wheaton tube, with agitation and under an argon atmosphere. The agitation is maintained at AT for 24 h. The reaction medium is directly evaporated to dryness. The crude is chromatographed on a silica cartridge (12 g, eluent EtOAc). 92 mg of expected product Ex5 (white solid) are obtained.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07994162B2
Source dataset	uspto-grants-2011_08
ORD ID	ord-1b8b6117e03245e59d1b710a285ec006
Source note	uspto-grants-2011_08