Hydrochloric Acid → HCID 86691115, compound

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
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	1-Amino-1-cyclopropanecarbonitrile hydrochloride	HCID 14586363	—
Reactant	N-(tert-Butoxycarbonyl)-3-chloro-L-tyrosine	HCID 21970632	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 86691115	HCID 86691115	—

Reaction Conditions

Temperature	25 °C

Reaction Steps

(S)-2-(tert-butoxycarbonylamino)-3-(3-chloro-4-hydroxyphenyl)propanoic acid (3.86 g, 12.2 mmol, Eq: 1.00) was dissolved in DMF (50 mL). HATU (9.3 g, 24.4 mmol, Eq: 2.00), 1-amino-1-cyclopropanecarbonitrile hydrochloride (1.74 g, 14.7 mmol, Eq: 1.20) and Hunig's Base (3.16 g, 4.27 mL, 24.4 mmol, Eq: 2.00) were added to the obtained suspension. The reaction mixture was stirred at 25° C. for 24 h. The reaction mixture was poured into aqueous 0.1M HCl (300 mL), extracted with dichloromethane (3×125 mL), dried over Na2SO4, filtered and evaporated. The crude material was purified by flash chromatography (silica gel, 80 g, 0% to 65% AcOEt in n-heptane) to yield a white solid (3.13 g; 67%). m/z=378.1 [M−H]−.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09290467B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-860ba563972f4e1ea949f1cf1be4add3
Source note	uspto-grants-2016_03