Patent ID: 7518017

Claim:
A method of synthesizing a fenicol compound of formula (VI): wherein each Y and Y 1 is independently —H; —SO 2 R 1 ; —S(O)R 1 —SR 1 ; —S(O)NH 2 ; —SO 2 NH 2 ; —S(O)NHR 1 ; —S(O)NHR 1 ; —S(O)N(R 1 ) 2 ; —S(O)N(R 1 ) 2 ; —C(O)R 1 ; —C(O)OR 1 ; —OC(O)R 1 ; —OR 1 ; —R 1 ; —CN; halogen; —NO 2 ; —NH 2 ; —NHR 1 ; —NH(R 1 ) 2 ; —C(O)NH 2 ; —C(O)NHR 1 ; —C(O)N(R 1 ) 2 ; phenyl; or phenyl substituted with halogen; —NO 2 , —SO 2 R 1 , —OR 1 , or —R 1 , each R 1 is independently a C 1 -C 4 hydrocarbon group, R 2 is —CH 3 , —CH 2 F, or —CH 2 OP, P is a hydroxyl protecting group, R 3 is a —C 1 -C 4 hydrocarbon group, —CH 2 F, —CHF 2 , —CF 3 , —CH 2 Cl, —CHCl 2 , —CCl 3 , —CH 2 Br, —CHBr 2 , —CBr 3 , —CH 2 I, —CHI 2 , —CI 3 , —CH 2 CN, —CH 2 N 3 , —CH 2 SO 2 CH 3 , —CZ 2 CZ 3 , —CH(CH 3 )(CF 3 ), —CH(OH)(CH 3 ), —CH(CF 3 ) 2 , —CH(CF 3 )Z, and —CH(CF 3 )OH; and each Z is independently a hydrogen or halogen, comprising the steps of: (i) converting an amino acid of formula (V): to a N-trifluoroacetylated amino acid of formula (IV): (ii) converting the N-trifluoroacetylated amino acid of formula (IV) to a compound of formula (III): wherein X is a halide; (iii) contacting the compound of formula (III) with a compound of formula (II): to provide a compound of formula (I): (iv) contacting the compound of formula (I) with a reducing agent to provide a compound of formula (VII): (v) converting the compound of formula (VII) to a compound of formula (VIII): (vi) converting the compound of formula (VIII) to a compound of formula (VI).