Benzene → tert-butyl 2-[({(2R,3S)-2-hydroxy-3-[((2S)-3-methyl-2-{3-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl}butanoyl)amino]-4-phenylbutyl}amino)methyl]pyrrolidine-1-carboxylate

참여 물질

역할	이름	HCID	투입량
반응물	Benzene	HCID 241	—
반응물	tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate	HCID 2734674	—
반응물	Sodium borohydride	HCID 4311764	—
반응물	(2S)-N-[(1S,2R)-3-amino-1-benzyl-2-hydroxypropyl]-3-methyl-2-{3-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl}butanamide	HCID 66891621	—
용매	Ethanol	HCID 702	—
생성물	tert-butyl 2-[({(2R,3S)-2-hydroxy-3-[((2S)-3-methyl-2-{3-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl}butanoyl)amino]-4-phenylbutyl}amino)methyl]pyrrolidine-1-carboxylate	HCID 66891972	103%

반응 조건

온도	70 °C

반응 단계

A solution of the product of Example 274C (59 mg) in ethanol:benzene (1 mL, 1:1) was treated with N-t-butoxylcarbonyl-(L)-prolinal (26 mg, 1 equivalent), stirred at 70° C. for 1 hour, cooled at 25° C., treated with NaBH4 (14 mg, 3 equivalents) at 25° C. and stirred for 16 hours. The mixture was quenched with saturated NH4Cl and partitioned between water and ethyl acetate. The organic layer was separated, dried over MgSO4, filtered and concentrated to give 85 mg of the crude title compound.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08653141B2
출처 데이터셋	uspto-grants-2014_02
ORD ID	ord-2a70caf09ac248f280655a122148fd93
출처 메모	uspto-grants-2014_02