Cesium carbonate → (2R,5R)-5-{(1S,2S)-2-Acetylamino-3-[3-(2,2-difluoroethoxy)-phenyl]-1-hydroxypropyl}-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester

https://huagongshe.com/de/reaction/20429

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Cesium carbonate	HCID 10796	—
Edukt	2-Bromo-1,1-difluoroethane	HCID 136186	—
Edukt	(2R,5R)-5-[(1S,2S)-2-Acetylamino-1-hydroxy-3-(3-hydroxyphenyl)-propyl]-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester	HCID 68562669	—
Lösungsmittel	Dimethylformamide	HCID 6228	—
Lösungsmittel	Ethyl Acetate	HCID 8857	—
Produkt	(2R,5R)-5-{(1S,2S)-2-Acetylamino-3-[3-(2,2-difluoroethoxy)-phenyl]-1-hydroxypropyl}-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester	HCID 58972247	—

Reaktionsbedingungen

Temperatur	60 °C

Reaktionsschritte

Dissolve (2R,5R)-5-[(1S,2S)-2-acetylamino-1-hydroxy-3-(3-hydroxyphenyl)-propyl]-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester (204 mg) and 2,2-difluoro-1-bromoethane (0.065 mL) and cesium carbonate (391 mg) in N,N-dimethylformamide (5 mL) and heat to 60° C. for 18 hours. Dilute with ethyl acetate, wash with saturated aqueous sodium chloride, dry and purify (silica gel chromatography, eluting with 1:1 ethyl acetate:dichloromethane), to give the desired compound (223 mg).

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US07745438B2
Quelldatensatz	uspto-grants-2010_06
ORD ID	ord-50f5559b755c41c4bb23b87a638117e2
Quellennotiz	uspto-grants-2010_06