Triethylamine → Methyl phenylacetate

Temperature

0 °C

A mixture of 2.74 g (80 mmol) 1-(3,4-dimethoxy-phenyl)-3-(4-trifluoromethyl-phenyl)-propan-1-ol, 1.1 g (9.6 mmol) methanesulfonylchloride and 2.44 g (24 mmol) NEt3 in 60 mL diethyl ether was stirred at 0° C. for 1 h. 3.25 g (16 mmol) (S)-2-phenylglycine methyl ester hydrochloride, and 2.44 g (24 mmol) NEt3 and 30 mL THF was added. The mixture was stirred at 0° C. for 1 h and 16 h at room temperature. Water was added and the mixture was extracted with ethyl acetate. The combined organic fractions were washed with water, dried with MgSO4 and evaporated to dryness. The residue was purified by flash column chromatography on silica eluting with a gradient formed from ethyl acetate and heptane. The product containing fractions were evaporated to dryness to yield 0.97 g (S)-[(S or R)-1-(3,4-dimethoxy-phenyl)-3-(4-trifluoromethyl-phenyl)-propylamino]-phenyl-acetic acid methyl ester (MS (m/e): 488.0 (MH+)) as yellow oil and 0.91 g (S)-[(R or S)-1-(3,4-Dimethoxy-phenyl)-3-(4-trifluoromethyl-phenyl)-propylamino]-phenyl-acetic acid methyl ester (MS (m/e): 488.0 (MH+)) as yellow oil.

1. stirringThe mixture was stirred at 0° C. for 1 h and 16 h at room temperature
2. extractionthe mixture was extracted with ethyl acetate
3. washThe combined organic fractions were washed with water
4. dry with materialdried with MgSO4
5. customevaporated to dryness
6. customThe residue was purified by flash column chromatography on silica eluting with a gradient
7. customformed from ethyl acetate and heptane
8. additionThe product containing fractions
9. customwere evaporated to dryness

ORD record

ord-14b62e50f7a948c0ba02c3fcdccf5d70

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07829563B2