Diisopropylethylamine → HCID 71245383, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methyl threoninate	HCID 2734894	—
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	HCID 15282610	HCID 15282610	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 71245383	HCID 71245383	74.8%

Reaction Steps

To a suspension of compound 3 (1.0 g, 2.94 mmol), L-threonine methyl ester (471 mg, 3.53 mmol) in DMF (20 mL) was added HATU (1.12 g, 2.94 mmol) and DIPEA (1.58 mL, 8.84 mmol) at 5° C. The reaction mixture was stirred at RT for 16 h. It was diluted with EtOAc (150 mL) and washed with water (2×30 mL). The organic layer was washed with brine, dried over Na2SO4, concentrated and purified by silica gel column chromatography 50% EtOAc/Hexane as eluent to yield compound 4 (1.0 g, 74%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08673843B2
Source dataset	uspto-grants-2014_03
ORD ID	ord-4fb2abf2e9144a2dafe2a8cab802dadf
Source note	uspto-grants-2014_03