Processes for the synthesis of diprotected R[R*,S*]-3,5-dihydroxy-6-oxohexanoate esters

US4870199A · kind A · utility

Assignee

• Sandoz Pharm. Corp. · US

Inventors

• Kau-Ming Chen · Dover, US
• Goetz E. Hardtmann · Florham Park, US
• Prasad Koteswara Kapa · Parsippany, US
• George Tien-San Lee · Bloomfield, US
• Jerome Linder · Westfield, US
• Sompong Wattanasin · Waltham, US

Key dates

• Filing date: Mar 10, 1988
• Grant date: Sep 26, 1989
• Expiry date: Mar 10, 2008

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Process for the synthesis of compounds of the formula ##STR1## in R[R*,S*] enantiomeric form, wherein each P.sub.1 is independently an hydroxy group-protecting group, and PA0 R.sub.2z is C.sub.1-4 alkyl, benzyl or allyl, comprising, as a key step when R.sub.2z is R.sub.2x, the reaction of the compound of the formula ##STR2## in (S) enantiomeric form with a compound of the formula EQU Mg.sup. .circle.+2 (.sup..crclbar. OOC--CH.sub.2 --COOR.sub.2x).sub.2 to obtain a compound of the formula ##STR3## in (S) enantiomeric form, and, as a key step when R.sub.2z is R.sub.2y, the reaction of a compound of the formula ##STR4## in (S) enantioimeric form with a compound of the formula EQU Li.sup..sym..crclbar. CH.sub.2 --COOR.sub.2y to obtain a compound of the formula ##STR5## in (S) enantiomeric form, wherein R.sub.2x is primary or secondary C.sub.1-4 alkyl, benzyl or allyl, PA0 R.sub.2y is C.sub.1-4 alkyl not containing an asymmetric carbon atom, and PA0 R.sub.3 ' is methyl or ethyl, processes for the synthesis of compounds of the formula ##STR6## comprising reacting a compound of the formula ##STR7## with the reaction product of a strong base and a compound of the formula ##STR8## optionall…