Ethyl Acetate → HCID 86650245, compound

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Diisobutylaluminum hydride	HCID 14487	—
Reactant	(7S,10S,13S)-10-Isopropyl-9,12-dioxo-13-[(1H-pyrrole-2-carbonyl)-amino]-2-oxa-8,11-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-triene-7-carboxylic acid methyl ester	HCID 66846964	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 86650245	HCID 86650245	—

Reaction Conditions

Temperature	-78 °C

Reaction Steps

Ester 51 (45 mg) was dissolved in DCM (6 mL) under an atmosphere of argon. The reaction was cooled to −78° C. To the resultant solution DIBAL (0.5 mL) was added dropwise. This was stirred for 2 h before being allowed to warm to rt overnight. The reaction mixture was partitioned between EtOAc and 1M hydrochloric acid. The aqueous phase was extracted again with EtOAc and the combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification was achieved using flash chromatography, eluting with a gradient of 1/1 EtOAc/(50/70) petroleum ether to EtOAc to yield a light brown solid, 14 mg, 33%. Rf=0.25 (1/1 EtOAc/(50/70) petroleum ether).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09434762B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-375ca76d596546619024bda213980444
Source note	uspto-grants-2016_09