Lithium hydroxide, monohydrate → 2-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4-hydroxy-5-(benzylthio)-pentanoic Acid

To a solution of 3-[(4′-methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-2-oxo-5-[(benzylthio)methyl]-tetrahydrofuran 17a (40 mg, 0.083 mmol) in water (3 mL) and THF (3 mL) is added slowly lithium hydroxide monohydrate (35 mg, 0.82 mmol). The reaction mixture is stirred overnight, then concentrated to dryness. The resulting mixture is diluted with water, and then the mixture is extracted twice with Et2O. The Et2O layer is discarded and the aqueous layer is neutralized carefully with 1N HCl to pH 6, then extracted three times with EtOAc. The combined EtOAc layer is washed with brine, dried over MgSO4 and concentrated to a solid which is recrystallized from EtOAc/hexane (1:4) to give the desired product as a white solid.

1. concentrationconcentrated to dryness
2. additionThe resulting mixture is diluted with water
3. extractionthe mixture is extracted twice with Et2O
4. extractionextracted three times with EtOAc
5. washThe combined EtOAc layer is washed with brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated to a solid which
8. customis recrystallized from EtOAc/hexane (1:4)

ORD record

ord-e17cb121664642bd8fe7129f80e103f3

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06566381B1