(+)-L-Leucine methyl ester → HCID 2752558, compound

Participants

Role	Name	HCID	Charge
Reactant	(+)-L-Leucine methyl ester	HCID 65105	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-	HCID 77857	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 2752558	HCID 2752558	83.3%

Reaction Steps

Boc-Phe-OH (2 g, 13.77 mmol), H-Leu-OMe (11 g, 41.32 mmol), HOBt (5.58 g, 41.32 mmol), and HBTU (15.67 g, 41.32 mmol) were dissolved in DMF (69 mL) and then DIPEA (7.2 mL, 41.32 mmol) was added under argon. The reaction was stirred for 8 hrs at room temperature. The reaction was extracted by EtOAc and wash with 5% NaHSO3, sat. NaHCO3 and brine. The organic layer was dried over Na2SO4, and concentrated by rotary evaporation. The crude was purified by chromatography (silica, 4/1: Hexane/EtOAc, Rf=0.3) to give methyl 2-(2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoylamino)-4-methylpentanoate as white solid (4.5 g, 8%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08895497B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-05f93802438047d095fbc352b48933c1
Source note	uspto-grants-2014_11