Water → HCID 70540935, compound

Reaction equation

[CH2:1]([N:3]([C@@H:8]1[CH2:14][CH2:13][CH2:12][C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[C@H:9]1[OH:19])[C:4](=[O:7])[CH2:5]Cl)[CH3:2].[H-].[Na+].O>CN(C)C=O>[CH2:1]([N:3]1[C:4](=[O:7])[CH2:5][O:19][C@@H:9]2[C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[CH2:12][CH2:13][CH2:14][C@@H:8]12)[CH3:2]

Participants

Procedure

The residue from Step A was dissolved in 50 ml of dimethyl formamide and added dropwise to a solution of 0.7 g (0.0146 m) of a 50% oil dispersion of sodium hydride in 50 ml of dimethyl formamide with stirring. After stirring one hour, excess sodium hydride was decomposed by the addition of water. The mixture was extracted twice with ethyl acetate and the extract was back washed with water, dilute, cold hydrochloric acid and saturated aqueous sodium bicarbonate solution. After drying (Na2SO4) the ethyl acetate solution was concentrated to dryness in vacuo to provide crude product.