2-(tert-butyldiphenylsilyloxy)-N-methylethanamine → (R)-N-(2-(tert-butyldiphenylsilyloxy)ethyl)-N-methyl-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanamide

Participants

Role	Name	HCID	Charge
Reactant	2-(tert-butyldiphenylsilyloxy)-N-methylethanamine	HCID 11823158	—
Reactant	(R)-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoic acid	HCID 66723519	—
Reactant	(R)-N-(2-(tert-Butyldiphenylsilyloxy)ethyl)-N-ethyl-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluorom ethylsulfonyl)phenylamino)butanamide	HCID 66723918	—
Product	(R)-N-(2-(tert-butyldiphenylsilyloxy)ethyl)-N-methyl-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanamide	HCID 66723792	93%

Reaction Steps

The title product (590 mg, yield: 93%) was prepared using a procedure similar to the one described for the synthesis of INTERMEDIATE 24 utilizing (R)-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoic acid (INTERMEDIATE 8, 400 mg, 0.8 mmol) and 2-(tert-butyldiphenylsilyloxy)-N-methylethanamine (INTERMEDIATE 26, 251 mg, 0.8 mmol) as starting materials. The title product was purified by column chromatography (ISCO, 12 g silica gel column, eluting with 0→100% EtOAc/hexanes).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09248140B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-55969b53cf26457d856974f075b7df12
Source note	uspto-grants-2016_02