Tert-Butylamine → (S)-[2-[(1,1-dimethylethyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-carbamic acid 1,1-dimethylethyl ester

Participants

Role	Name	HCID	Charge
Reactant	Tert-Butylamine	HCID 6385	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine	HCID 98763	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Solvent	Diethyl Ether	HCID 3283	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(S)-[2-[(1,1-dimethylethyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-carbamic acid 1,1-dimethylethyl ester	HCID 11809380	153.7%

Reaction Conditions

Temperature	0 °C

Reaction Steps

A solution of N-(tert-Butyloxycarbonyl)-O-benzyl-L-tyrosine (Bachem, 2.00 g, 5.38 mmol) in 20 mL of DMF was cooled to 0C and treated with iPr2NEt (1.5 mL) followed by HBTU (2.04 g, 5.38 mmol). The resulting suspension was stirred for 30 minutes at 0° C. and then treated with tert-butylamine (0.48 g, 6.56 mmol). The reaction mixture was stirred for 1 hour at 0° C. and warmed to room temperature. The reaction mixture was poured into Et2O and washed sequentially with saturated aqueous NaHCO3 solution, and saturated aqueous NaCl solution. The organic phase was dried (MgSO4), filtered, and concentrated. The crude residue was purified by chromatography (silica gel, 3:1 heptane/ethyl acetate) to give the product (2.65 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06423689B1
Source dataset	uspto-grants-2002_07
ORD ID	ord-62054830a605401f9c70966e633748bd
Source note	uspto-grants-2002_07