Hydrochloric Acid → HCID 86691114, compound

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	tert-Butyl Formate	HCID 61207	—
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	(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(prop-2-en-1-yloxy)phenyl]propanoic acid	HCID 10853202	—
Reactant	1-Amino-1-cyclopropanecarbonitrile hydrochloride	HCID 14586363	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 86691114	HCID 86691114	—

Reaction Conditions

Temperature	25 °C

Reaction Steps

(S)-3-(4-(allyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoic acid (5 g, 15.6 mmol, Eq: 1.00) was dissolved in DMF (30 ml). HATU (11.8 g, 31.1 mmol, Eq: 2.00), Hunig's Base (4.02 g, 5.43 ml, 31.1 mmol, Eq: 2.00) and 1-amino-1-cyclopropanecarbonitrile hydrochloride (2.21 g, 18.7 mmol, Eq: 1.20) were added to the above suspension and stirred at 25° C. for 24 h. The reaction mixture was poured into 0.1M HCl (250 mL) and extracted with AcOEt (3×75 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was dissolved in CH2Cl2 (10 mL), 2 minutes later it began to precipitate. The suspension was filtered. The filtered solution was purified by flash chromatography (silica gel, 80 g, 0% to 90% AcOEt in heptane) to yield a light yellow solid (3.0 g; 50%). m/z=286.1 [M+H-Boc]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09290467B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-3f3094969fbf4bddb69768e4b975708f
Source note	uspto-grants-2016_03