Ethyl Acetate → HCID 66847153, compound

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
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	(S)-2-[(S)-3-(4-But-3-enyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-4-methyl-pentanoic acid	HCID 66847077	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 66847153	HCID 66847153	—

Reaction Steps

Carboxylic acid 21 (2.14 g, 4.77 mmol), HATU (2.00 g, 5.25 mmol) and (S)-allyl-glycine methyl ester hydrochloride (0.870 g, 5.25 mmol) were dissolved in DMF (30 mL). DIPEA was added (3.32 mL, 19.1 mmol) and the reaction mixture was stirred at rt for 18 h before being partitioned between EtOAc and 1M hydrochloric acid. The organic phase was washed sequentially with 1M hydrochloric acid and brine before being dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether to yield a white solid, 2.24 g, 84%. Rf=0.32 (1/1 EtOAc/(50/70) petroleum ether). m.p. 166-168° C.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09434762B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-8733e473152a41e591953f999b28f39c
Source note	uspto-grants-2016_09