Triethylamine → N-[[1,2,3,4-Tetrahydro-2-[[(t-butyl)thio]methyl]-2-naphthalenyl]carbonyl]-L-alanine, benzyl ester

참여 물질

역할	이름	HCID	투입량
반응물	Triethylamine	HCID 8471	—
반응물	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
반응물	L-Alanine, phenylmethyl ester, hydrochloride (1:1)	HCID 12210893	—
반응물	2-Carboxy-2-(t-butyl)thiomethyl-1,2,3,4-tetrahydronaphthalene	HCID 19789937	—
용매	Tetrahydrofuran	HCID 8028	—
생성물	N-[[1,2,3,4-Tetrahydro-2-[[(t-butyl)thio]methyl]-2-naphthalenyl]carbonyl]-L-alanine, benzyl ester	HCID 131718217	48%

반응 단계

Dissolve 2-carboxy-2-(t-butyl)thiomethyl-1,2,3,4-tetrahydronaphthalene (278 mg, 1.0 mmol) in anhydrous tetrahydrofuran (10 mL). Add 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (230 mg, 1.2 mmol), L-alanine benzyl ester hydrochloride (216 mg, 1.00 mmol) and triethylamine (0.132 mL, 1.00 mmol). Stir at room temperature under an argon atmosphere overnight. Partition between ethyl ether and 5% sulfuric acid. Separate the organic phase and wash with water, saturated sodium hydrogen carbonate and brine. Dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography (20% ethyl acetate/hexane) to give the title compound as a clear yellow oil (210 mg, 48%).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US05252601
출처 데이터셋	uspto-grants-1993_10
ORD ID	ord-c3345879c2334a04a2e5143786208055
출처 메모	uspto-grants-1993_10