N-(tert-butoxycarbonyl)glycine → ethyl N-(tert-butoxycarbonyl)glycyl-3-methoxyphenylalaninate

https://huagongshe.com/reaction/1972546

Participants

Role	Name	HCID	Charge
Reactant	N-(tert-butoxycarbonyl)glycine	HCID 78288	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	ethyl (2S)-2-amino-3-(3-methoxyphenyl)propanoate	HCID 8027297	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	ethyl N-(tert-butoxycarbonyl)glycyl-3-methoxyphenylalaninate	HCID 66582631	91.9%

Reaction Steps

To a 100-mL round-bottomed flask was added ethyl 3-methoxyphenylalaninate (526 mg, 2.35 mmol), 2-(tert-butoxycarbonylamino)acetic acid (454 mg, 2.59 mmol, Sigma-Aldrich, St. Louis, Mo.), HATU (1.07 g, 2.82 mmol, Sigma-Aldrich, St. Louis, Mo.), Hünig's base (0.819 mL, 4.71 mmol) and DMF (5 mL). The reaction mixture was stirred at room temperature for 2 h then diluted with water (30 mL) and extracted with EtOAc (2×50 mL). The organic extract was washed with saturated aqueous NaCl (30 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as light-yellow oil. The crude product was purified by silica gel chromatography, eluting with 60% EtOAc in hexanes to give ethyl N-(tert-butoxycarbonyl)glycyl-3-methoxyphenylalaninate (822 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08431563B2
Source dataset	uspto-grants-2013_04
ORD ID	ord-2dcd9ca70385444abfcc1629340b43f6
Source note	uspto-grants-2013_04