Trifluoroacetic acid → Bisegliptin

Participants

Role	Name	HCID	Charge
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	Methanesulfonic anhydride	HCID 81560	—
Reactant	(2S,4S)-1-[2-[(4-ethoxycarbonylbicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carboxamide	HCID 46854534	—
Product	Bisegliptin	HCID 11688894	71%

Reaction Steps

Using (2S,4S)-1-[2-[(4-ethoxycarbonylbicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carboxamide (500 mg), methanesulfonic anhydride (248 mg) as a dehydrating agent and trifluoroacetic acid (0.11 mL) as an acid, a white powder of (2S,4S)-1-[2-[(4-ethoxycarbonylbicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile was obtained (obtained amount: 340 mg, yield: 71%) by the same method of Example 1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08143427B2
Source dataset	uspto-grants-2012_03
ORD ID	ord-64364973f0d542278885e1680d475a2c
Source note	uspto-grants-2012_03