反応 #500553

反応方程式

3-[(4′-Methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-2-oxo-5-[(phenylamino)methyl]-tetrahydrofuran

lithium hydroxide monohydrate

→

desired product

2-[(4′-Methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-4-hydroxy-5-(phenylamino)-pentanoic acid

溶媒

water

THF

反応条件

後処理

1. 1
   濃縮concentrated to dryness
2. 2
   workup.ADDITIONThe resulting mixture is diluted with water
3. 3
   抽出the mixture is extracted twice with Et2O
4. 4
   抽出extracted three times with EtOAc
5. 5
   洗浄The combined EtOAc layer is washed with brine
6. 6
   乾燥dried over MgSO4
7. 7
   濃縮concentrated to a solid which
8. 8
   その他is recrystallized from EtOAc/hexane (3:7)

実験手順

To a solution of 3-[(4′-Methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-2-oxo-5-[(phenylamino)methyl]-tetrahydrofuran 19a (0.19 g, 0.42 mmol) in water (3 mL) and THF (3 mL) is added slowly lithium hydroxide monohydrate (180 mg, 4.2 mmol). The reaction mixture is stirred for 4 h, and 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 (3:7) to give the desired product as a white solid.

出典