Tetrabutylammonium Fluoride → 4-[(S)-2-({5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-5-hydroxy-pentanoyl]-piperazine-1-carboxylic acid butyl ester

To solution of 400 mg 4-[(S)-2-({5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-5-(tert-butyl-diphenyl-silanyloxy)-pentanoyl]-piperazine-1-carboxylic acid butyl ester in 40 ml THF were added 0.6 ml TBAF (1 M in THF) and the solution was stirred for 12 h. The reaction mixture was concentrated, the residue dissolved in dichloromethane and extracted with water (3×). The organic layer was evaporated and the residue purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA). The fractions containing the product were lyophilized to yield the pure product.

1. concentrationThe reaction mixture was concentrated
2. dissolutionthe residue dissolved in dichloromethane
3. extractionextracted with water (3×)
4. customThe organic layer was evaporated
5. customthe residue purified by preparative HPLC (
6. washC18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA)
7. additionThe fractions containing the product
8. customto yield the pure product

ORD 기록

ord-53bde2bfa34441ca9394da21e6913750

출처 데이터셋

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08426420B2