L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → tert-butyl N-[(1S)-2-phenyl-1-(prop-2-yn-1-ylcarbamoyl)ethyl]carbamate

Participants

Role	Name	HCID	Charge
Reactant	L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-	HCID 77857	—
Reactant	Propargylamine	HCID 239041	—
Reactant	(S)-2-((2S,4R)-1-((S)-2-((S)-2-((tert-Butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-4-((S)-2-((S)-2-((S)-2-((tert-butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)pyrrolidine-2-carboxamido)-3-phenylpropanoic acid	HCID 86705917	—
Product	tert-butyl N-[(1S)-2-phenyl-1-(prop-2-yn-1-ylcarbamoyl)ethyl]carbamate	HCID 11673861	99%

Reaction Steps

Following a procedure analogous to that for the synthesis of Compound D of Example 1, (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid (Aldrich, 355 mg, 1.34 mmol) and prop-2-yn-1-amine (Combi-Blocks, 86 μL, 1.34 mmol) were converted to the title compound (401 mg, 99%). 1H NMR (CDCl3) δ 7.39-7.16 (m, 5H), 6.01 (br s, 1H), 4.97 (br s, 1H), 4.33 (d, J=7.0 Hz, 1H), 4.07-3.84 (m, 2H), 3.08 (d, J=6.8 Hz, 2H), 2.20 (t, J=2.5 Hz, 1H), 1.47-1.33 (m, 9H); MS (ESI+) m/z 303.3 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08889712B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-bc2121b840c04b13925572e865ca1887
Source note	uspto-grants-2014_11