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

To a solution of [3-(2-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazol-5-yl)-2-ethylphenyl]acetaldehyde (D78) (160 mg), acetic acid (0.036 mL) and sodium acetate (51.0 mg) in ethanol (20.00 mL) stirred under nitrogen at room temperature was added methyl 3-azetidinecarboxylate hydrochloride (182 mg) in one charge. The reaction mixture was stirred at room temperature for 30 min, then the solvent was evaporated in vacuo. The residue was dissolved in dichloromethane (DCM) (20 mL), sodium triacetoxyborohydride (165 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)-2-ethylphenyl]ethyl}-3-azetidinecarboxylate (D90) (200 mg) as a brown oil. The crude product was used for next step without further purification. MS (ES): C27H31ClN2O3S requires 498. found 499.2 (M+H+).

1. additioncharge
2. customthe solvent was evaporated in vacuo
3. dissolutionThe residue was dissolved in dichloromethane (DCM) (20 mL)
4. additionsodium triacetoxyborohydride (165 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 record

ord-9a36b5603dfe4eb9955909b7be7e196c

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389508B2