Methyl iodide → {4-[1-Methyl-2-oxo-2-(3-trifluoromethyl-phenyl)-ethylcarbamoyl]-cyclohexylmethyl}-carbamic acid benzyl ester

This compound was prepared using a procedure similar to the one described by Moriya et. al. (J. Med. Chem. (1986) 29:333–341) for the alkylation of α-(N-acylamino) ketones: {4-[2-Oxo-2-(3-trifluoromethyl-phenyl)-ethylcarbamoyl]-cyclohexylmethyl}-carbamic acid benzyl ester (From Example 1A; 584 mg, 1.23 mmol) was dissolved in dry DMF and brought to −40° C. using a dry ice/acetonitrile cooling bath. NaH (61 mg, 1.53 mmol, 60% dispersion in oil) was added in one portion and the mixture was stirred for 15 minutes. MeI (192 mg, 1.35 mmol) was added all at once, the cooling bath was removed and the reaction mixture was allowed to come to room temperature. An excess of saturated aqueous NH4Cl solution was added and the resulting mixture extracted with EtOAc. The EtOAc layer was washed sequentially with 3N HCl, NaHCO3 (sat'd), and brine. The solution was dried (Na2SO4) and concentrated under reduced pressure to give {4-[1-Methyl-2-oxo-2-(3-trifluoromethyl-phenyl)-ethylcarbamoyl]-cyclohexylmethyl}-carbamic acid benzyl ester.

1. customThis compound was prepared
2. custombrought to −40° C.
3. customwas removed
4. customto come to room temperature
5. additionAn excess of saturated aqueous NH4Cl solution was added
6. extractionthe resulting mixture extracted with EtOAc
7. washThe EtOAc layer was washed sequentially with 3N HCl, NaHCO3 (sat'd), and brine
8. dry with materialThe solution was dried (Na2SO4)
9. concentrationconcentrated under reduced pressure

ORD record

ord-410f8339ee9f45aca1845b672c228cc4

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07034034B2