Acetic Acid → Methyl 1-{2-[3-(2-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazol-5-yl)-5-fluoro-2-(methyloxy)phenyl]ethyl}-3-azetidinecarboxylate

To a solution of [3-(2-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazol-5-yl)-5-fluoro-2-(methyloxy)phenyl]acetaldehyde (D80) (95 mg), acetic acid (0.044 mL) and sodium acetate (113 mg) in ethanol (20.00 mL) stirred under nitrogen at room temperature was added methyl 3-azetidinecarboxylate (106 mg) in one charge. The reaction mixture was stirred at room temperature for 1 h, then the solvent was evaporated in vacuo. The residue was dissolved in dichloromethane (DCM) (20 mL), sodium triacetoxyborohydride (195 mg) was added to the mixture. The reaction mixture was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate (100 mL) and saturated brine (30 mL). The organic phase was dried over sodium sulphate and evaporated in vacuo to give the crude product methyl 1-{2-[3-(2-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazol-5-yl)-5-fluoro-2-(methyloxy)phenyl]ethyl}-3-azetidinecarboxylate (D82) (100 mg). The crude product was used for next step without further purification. MS (ES): C26H28ClFN2O4S requires 518. found 519.2 (M+H+).

1. additioncharge
2. customthe solvent was evaporated in vacuo
3. dissolutionThe residue was dissolved in dichloromethane (DCM) (20 mL)
4. additionsodium triacetoxyborohydride (195 mg) was added to the mixture
5. stirringThe reaction mixture was stirred at room temperature overnight
6. customThe reaction mixture was partitioned between ethyl acetate (100 mL) and saturated brine (30 mL)
7. dry with materialThe organic phase was dried over sodium sulphate
8. customevaporated in vacuo

ORD 기록

ord-f6261b93c077450e9d5dc2c31ed4ab3b

출처 데이터셋

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08389508B2