Diisopropylethylamine → HCID 131728746, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	6-(3-Fluorophenyl)nicotinic acid	HCID 24729972	—
Reactant	Cis-(3R, 4S)-1-Boc-3-aMino-4-hydroxypyrrolidine	HCID 50986390	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 131728746	HCID 131728746	58%

Reaction Steps

To a solution of 6-(3-fluorophenyl)nicotinic acid (391 mg, 1.8 mmol ) in DMF (10 mL) at 0° C. was added HATU (753 mg, 1.98 mmol) and DIPEA (0.47 mL, 2.07 mmol ). After 15 min, cis-tert-butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate was added and the reaction stirred at room temperature for 5 hrs. The solvent was removed in vacuo and the residue diluted with ethyl acetate and water. The layers were separated and the organic layer washed with brine, dried (MgSO4) and the solvent removed to give an oil, which after chromatography (silica, 65% ethyl acetate:hex) to give the desired product, cis-tert-butyl-3-({[6-(3-fluorophenyl)pyridin-3-yl]carbonyl}amino)-4-hydroxypyrrolidine-1-carboxylate (420 mg, 58%). LC/MS (M+H)=401.9 observed, 402.18 expected.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07902373B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-e3a1b6b92c944483992250271f65838f
Source note	uspto-grants-2011_03