反应详情

A solution of 5-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-one (DE 3134590 A1) (150 mg) in dry DCM (2 ml) was treated with acetic acid and N-benzyl-6-(4-phenylbutoxy)hexan-1-amine (320 mg) (Tetrahedron Letters. 1994, 35, 9375) and stirred for 4 hr. Sodium triacetoxyborohydride (216 mg) was added and the reaction mixture stirred at room temperature for 3 days. Sodium borohydride (35 mg) in methanol (2 ml) was added and stirring continued for a further 2 h. The reaction mixture was quenched with water and partitioned between water and DCM. The organic phase was dried and concentrated in vacuo. The residue was purified by chromatography (Hexane-EtOAc, SPE) to give the title compound as a mixture with 5-(benzyloxy)-8-({benzyl[6-(4-phenylbutoxy)hexyl]amino}acetyl)-2H-1,4-benzoxazin-3(4H)-one (81.6 mg).

1. stirringthe reaction mixture stirred at room temperature for 3 days
2. stirringstirring
3. waitcontinued for a further 2 h
4. customThe reaction mixture was quenched with water
5. custompartitioned between water and DCM
6. customThe organic phase was dried
7. concentrationconcentrated in vacuo
8. customThe residue was purified by chromatography (Hexane-EtOAc, SPE)