Bristol-myers Squibb Compnay

Derron Ray Stark

Stephen R Baker

Bang-Chi Chen

Paul M Skonezny

Sandra L Quinlan

Brenda T Boyhan

Emerich Eisenreich

An economical process, amenable to large-scale production, is disclosed for the preparation of 2',3'-didehydro-3'-deoxythymidine (d4T) from 5-methyluridine. The process employs a novel, 5'-,acyl-2'.alpha.-halo-3'.alpha.-alkanesulfonylthymidine intermediate as well as a highly efficient and practical deprotection, isolation and purification procedure for the d4T product.

Preparation of 2',3'-didehydro-3'-deoxythymidine from 5-methyluridine

An improved process suitable for large-scale production of 2',3'-didehydro-3'-deoxythymidine (d4T) and close analogs is disclosed. The improved process yields d4T in high yield and purity without the use of hazardous reactions or reagents and incorporates several process improvements important on a large scale including a novel purification step involving the isolation of a d4T.N-methylpyrrolidinone solvate.

Process for large-scale preparation of

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Syracuse, NY, United States of America

Derron Ray Stark