Acetic Acid → tert-butyl(2S,3S)-2-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]amino}-3-methylpentanoate

참여 물질

역할	이름	HCID	투입량
반응물	Acetic Acid	HCID 176	—
반응물	Phthalylglycine aldehyde	HCID 76201	—
반응물	Sodium cyanoborohydride	HCID 5003444	—
반응물	tert-Butyl isoleucinate--hydrogen chloride (1/1)	HCID 11687228	—
용매	Methanol	HCID 887	—
생성물	tert-butyl(2S,3S)-2-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]amino}-3-methylpentanoate	HCID 66891692	61.7%

반응 조건

온도	25 °C

반응 단계

To a solution of Example 32A (12.1 g) in methanol (20 mL) was added L-isoleucine tert-butyl ester hydrochloride (13.0 g, 58 mmol), sodium cyanoborohydride (7.3 g, 116 mmol), and acetic acid (2 mL). The resulting solution was stirred for 3 hrs at 25° C. and the methanol removed under vacuum, dichloromethane (500 mL) added, and the solution extracted with aq. NaHCO3 (2×300 mL). Evaporation and purification of the organic layer gave 12.9 g of the title compound.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08653141B2
출처 데이터셋	uspto-grants-2014_02
ORD ID	ord-8ad332f9898f4d2c9e057c09c76d5c27
출처 메모	uspto-grants-2014_02