Bicarbonate Ion → (2R)-2-Phenylcarbonyloxypropyl(2S)-2-(tert-Butoxycarbonyl)amino-3-(3,4-dihydroxyphenyl)propanoate

関与物質

役割	名称	HCID	仕込み量
反応物	Bicarbonate Ion	HCID 769	—
反応物	N-methyl-2-pyrrolidone	HCID 13387	—
反応物	N-(tert-Buloxycarbonyl)-3,4-dihydroxy-L-phenylalanine	HCID 14217229	—
反応物	Boc-L-dopa tetrabutylammonium salt	HCID 131728417	—
溶媒	tert-Butyl methyl ether	HCID 15413	—
生成物	(2R)-2-Phenylcarbonyloxypropyl(2S)-2-(tert-Butoxycarbonyl)amino-3-(3,4-dihydroxyphenyl)propanoate	HCID 46899463	—

反応条件

温度	100 °C

反応手順

Boc-Dopa TBA salt 3 (50 g, 93 mmol), bicarbonate-washed (1R)-2-chloroisopropyl benzoate 5 (20 g, 100 mmol), and N-methylpyrrolidinone (NMP) (100 mL) were added to a 250 mL round bottom flask. The mixture was stirred under a nitrogen atmosphere and heated in an oil bath at 100° C. After ca. 72 hrs the reaction was cooled to room temperature, diluted with tert-butyl methylether (MTBE) (1 L), and washed twice with deionized water (2 L, then 1 L). The organic phase was separated, dried over anhydrous sodium sulfate (Na2SO4), filtered, and concentrated under reduced pressure to provide 35 g (76 mmol) of (2R)-2-phenylcarbonyloxypropyl(2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate 6 as a tan, viscous oil.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US09290445B2
出典データセット	uspto-grants-2016_03
ORD ID	ord-ac6d7a3090f84f31b3a45f1c609b470a
出典メモ	uspto-grants-2016_03