Triethylamine → (S)-2-[[[1-[[(S)-2-[[(1,1,-Dimethylethoxy)carbonyl]amino]-1-oxohexyl]amino]pentyl]methoxyphosphinyl]oxy-1-oxopropyl]-L-proline, ethyl ester

https://huagongshe.com/reaction/231944

関与物質

役割	名称	HCID	仕込み量
反応物	Triethylamine	HCID 8471	—
反応物	Pivaloyl chloride	HCID 62493	—
反応物	1-[(S)-6-[(Trifluoroacetyl)amino]-2-[[[1-[[(phenylmethoxy)carbonyl]amino]pentyl]methoxyphosphinyl]oxy]-1-oxohexyl]-L-proline, ethyl ester	HCID 131716004	—
反応物	1-[(S)-2-[[[(1-amino)pentyl]methoxyphosphinyl]oxy]-1-oxopropyl]-L-proline, ethyl ester	HCID 131716008	—
反応物	1-[(S)-2-[[[1-[[(S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxohexyl]amino]pentyl]methoxyphosphinyl]oxy]-1-oxopropyl]-L-proline, ethyl ester	HCID 131716009	—
溶媒	Acetic Acid	HCID 176	—
溶媒	Methanol	HCID 887	—
溶媒	Dichloromethane	HCID 6344	—
溶媒	Tetrahydrofuran	HCID 8028	—
生成物	(S)-2-[[[1-[[(S)-2-[[(1,1,-Dimethylethoxy)carbonyl]amino]-1-oxohexyl]amino]pentyl]methoxyphosphinyl]oxy-1-oxopropyl]-L-proline, ethyl ester	HCID 131716007	—

反応手順

N-[(1,1-Demethylethoxy)carbonyl]-L-norleucine (432 mg., 1.87 mmole) is dissolved in tetrahydrofuran (10 ml.) at room temperature under argon. The mixture is cooled to 0° and treated with triethylamine (0.66 ml., 4.56 mmole) and pivaloyl chloride (0.28 ml.). After one hour at 0°, the reaction mixture is treated with a solution of 1-[(S)-2-[[[(1-amino)pentyl]methoxyphosphinyl]oxy]-1-oxopropyl]-L-proline, ethyl ester (isomer B) (706 mg., 1.87 mmole) in tetrahydrofuran (10 ml.) according to the procedure of Example 4 part (e) to give 759 mg. of 1-[(S)-2-[[[1-[[(S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxohexyl]amino]pentyl]methoxyphosphinyl]oxy]-1-oxopropyl]-L-proline, ethyl ester (isomer B). TLC (silica gel; methylene chloride:methanol:acetic acid, 20:1:1) Rf =0.74.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US04849414
出典データセット	uspto-grants-1989_07
ORD ID	ord-1b9951ea3186438d81b1b0801d1304a6
出典メモ	uspto-grants-1989_07