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(1) Dissolve 100 grams of 3,5-difluorophenylacetic acid 1 in 500 mL of dichloromethane,Add 50 grams of thionyl chloride under stirring, and then increase the temperature to 40~50,After keeping this temperature for 4 hours, the reaction is completed by HPLC and TLC.Cool down, concentrate, add dichloromethane to dilute and store temporarily, as the prepared acid chloride;Add 500 mL of dichloromethane to another reaction flask,Then add 150g aluminum trichloride,Then add the previously prepared acid chloride dropwise to the reaction system,After the addition is complete, ethylene gas is introduced into the system,When the reaction of the raw materials is complete, add 500 mL of purified water to the system to quench the reaction.After quenching, the system is separated and the organic phase is concentrated.Intermediate 2 was obtained by column chromatography with a yield of 80%;
aluminium trichloride; In dichloromethane;
(Example 4) Synthesis of 6,8-difluoro-2-propyl-7-(3,4,5-trifluorophenyl)-9,10-dihydrophenanthrene Following conversion of (3,5-difluorophenyl)-acetic acid to an acid chloride with thionyl chloride, subsequent reaction with ethylene gas at -10C using methylene chloride as the solvent and in the presence of aluminum chloride yielded 5,7-difluoro-3,4-dihydro-1H-naphthalen-2-one.
aluminium trichloride; In dichloromethane;
Following conversion of (3,5-difluorophenyl)-acetic acid to an acid chloride with thionyl chloride, subsequent reaction with ethylene gas at -10C using methylene chloride as the solvent and in the presence of aluminum chloride yielded 5,7-difluoro-3,4-dihydro-1H-naphthalen-2-one.
L-norvalinyl-L-phenylglycine methyl ester hydrochloride[ No CAS ]
[ 105184-38-1 ]
[ 53308-95-5 ]
[ 78733-46-7 ]
N-[N-(3,5-difluorophenylacetyl)-L-norvalinyl]-L-phenylglycine methyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Example 253 Synthesis of N-[N-(3,5-Difluorophenylacetyl)-L-norvalinyl]-L-phenylglycine Methyl Ester Following General Procedure E and using 3,5-difluorophenylacetic acid (Aldrich) and L-norvalinyl-L-phenylglycine methyl ester hydrochloride (prepared from N-BOC-L-norvaline (Lancaster) and L-phenylglycine methyl ester hydrochloride (Aldrich) using General Procedure E, followed by removal of the BOC-group using General Procedure P), the title compound was prepared as a solid (mp=204-205° C.). The product was purified by flash chromatography using ethyl acetate/hexanes as the eluent.
L-norvalinyl-L-phenylglycine methyl ester hydrochloride[ No CAS ]
[ 105184-38-1 ]
[ 53308-95-5 ]
[ 78733-46-7 ]
N-[N-(3,5-Difluorophenylacetyl)-L-norvalinyl]-L-phenylglycine Methyl Ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
EXAMPLE 253 Synthesis of N-[N-(3,5-Difluorophenylacetyl)-L-norvalinyl]-L-phenylglycine Methyl Ester Following General Procedure E and using 3,5-difluorophenylacetic acid (Aldrich) and L-norvalinyl-L-phenylglycine methyl ester hydrochloride (prepared from N-BOC-L-norvaline (Lancaster) and L-phenylglycine methyl ester hydrochloride (Aldrich) using General Procedure E, followed by removal of the BOC-group using General Procedure P), the title compound was prepared as a solid (mp=204-205° C.). The product was purified by flash chromatography using ethyl acetate/hexanes as the eluent.
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