Hydrochloric Acid → (3R,4R)-4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

(3R,4R)-Methyl 4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylate (856 mg, 2.04 mmol) was stirred with 15% NaOH (5 mL) in THF (5 mL) and MeOH (5 mL) at 45° C. overnight. The mixture was then cooled to 0° C. and acidified with 2N HCl to pH ˜3. After extraction with ethyl acetate the organics were washed with brine, dried over MgSO4, and concentrated. The residue was triturated with ether to yield 726 mg (88%) of (3R,4R)-4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylic acid as a white solid. MS: (M+Na)+=428.0; (M−H)−=404.1.

Provenance & Evidence