Benzyloxycarbonyl-L-phenylalanine → benzyl (1S)-1-benzyl-2-[(3,3-diethoxypropyl)amino]-2-oxoethylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	Benzyloxycarbonyl-L-phenylalanine	HCID 70878	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1-Amino-3,3-diethoxypropane	HCID 521029	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	HCID 178418300	HCID 178418300	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	benzyl (1S)-1-benzyl-2-[(3,3-diethoxypropyl)amino]-2-oxoethylcarbamate	HCID 59065908	92%

Reaction Steps

By using an analogous procedure to that described for Reference Example 13, N-(carbobenzyloxy)-L-phenylalanine (2 g, 6.68 mmol), hydroxybenzotriazole (903 mg, 6.68 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride 1.28 g, 6.68 mmol), 1-amino-3,3-diethoxypropane (935 mg, 6.36 mmol) and N,N-diisopropylethylamine (1.16 mL, 6.68 mmol) were reacted in anhydrous tetrahydrofuran (32 mL) at room temperature for 16 h, to provide benzyl (1S)-1-benzyl-2-[(3,3-diethoxypropyl)amino]-2-oxoethylcarbamate (2.5 g, 92%) as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06858591B2
Source dataset	uspto-grants-2005_02
ORD ID	ord-d7e3ef9837ef482d892d5daff01e256a
Source note	uspto-grants-2005_02