John Dillo

US Patent:

6248882, Jun 19, 2001

Filed:

Oct 12, 2000

Appl. No.:

9/689209

Inventors:

Jolli Godfre - Trenton NJ
David R. Kronenthal - Yardley PA
Mark D. Schwinden - Holland PA
Sushil K. Srivastava - Dayton NJ
Keith Ramig - Orange NJ
John J. Venit - North Brunswick NJ
Paul A. Jass - Charles City IA
Saibaba Racha - East Syracuse NY
John Dillo - East Syracuse NY
Nachimuthu Soundararajan - Kendall Park NJ
Gerald L. Powers - North Brunswick NJ
Atul S. Kotnis - Kendall Park NJ

Assignee:

Bristol-Myers Squibb Co. - Princeton NJ

International Classification:

C07D26702

US Classification:

540490

Abstract:

The glycinamide of the formula ##STR1## is reacted with the dioxolane of the formula ##STR2## wherein L is a leaving group such as iodo, bromo, alkylsulfonyloxy, or arylsulfonyloxy to give the dioxolane of the formula ##STR3## Treating the dioxolane of formula III under aqueous refluxing conditions followed by exchanging the dioxolane acetal with a dimethoxy acetal and introduction of the methyl ester gives (S)-2-amino-6,6-dimethoxyhexanoic acid, methyl ester which is an intermediate in the preparation of the dual inhibitor [4S-[4. alpha. (R*),7. alpha. , 10a. beta. ]]-)octahydro-4-[(2-mercapto-1-oxo-3-phenylpropy)-amino]-5-oxo-7H -pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid. Also disclosed are storage stable salts of (S)-2-amino-6,6-dimethoxyhexanoic acid, methyl ester.

US Patent:

6329542, Dec 11, 2001

Filed:

Oct 12, 2000

Appl. No.:

9/689215

Inventors:

Jolli Godfre - Trenton NJ
David R. Kronenthal - Yardley PA
Mark D. Schwinden - Holland PA
Sushil K. Srivastava - Dayton NJ
Keith Ramig - Orange NJ
John J. Venit - North Brunswick NJ
Paul A. Jass - Charles City IA
Saibaba Racha - East Syracuse NY
John Dillo - East Syracuse NY
Nachimuthu Soundararajan - Kendall Park NJ
Gerald L. Powers - North Brunswick NJ
Atul S. Kotnis - Kendall Park NJ

Assignee:

Bristol-Myers Squibb Co. - Princeton NJ

International Classification:

C07C 6966

US Classification:

560186

Abstract:

The glycinamide of the formula ##STR1## is reacted with the dioxolane of the formula ##STR2## wherein L is a leaving group such as iodo, bromo, alkylsulfonyloxy, or arylsulfonyloxy to give the dioxolane of the formula ##STR3## Treating the dioxolane of formula III under aqueous refluxing conditions followed by exchanging the dioxolane acetal with a dimethoxy acetal and introduction of the methyl ester gives (S)-2-amino-6,6-dimethoxyhexanoic acid, methyl ester which is an intermediate in the preparation of the dual inhibitor [4S-[4. alpha. (R*),7. alpha. ,10a. beta. ]]-octahydro-4-[(2-mercapto-1-oxo-3-ph enylpropyl)-amino]-5-oxo-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid. Also disclosed are storage stable salts of (S)-2-amino-6, 6-dimethoxyhexanoic acid, methyl ester.