[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH3:7].[H-].CCOCC.[H][H].[CH2:16]([CH:24]1[CH2:26][CH:25]1[C:27]([O:29]CC)=O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].S(=O)(=O)(O)O>CCOCC>[CH2:16]([CH:24]1[CH2:26][CH:25]1[C:27]([NH2:7])=[O:29])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]4 g of lithium aluminum hydride was mixed with 300 ml of dry ether under a nitrogen blanket. Gaseous ammonia was liquefied by a dry ice condenser and the liquefied ammonia was dripped over a period of one hour onto the hydride/ether mixture until no further evolution of hydrogen was observed (7 g of ammonia used). 22.6 g of 1 was added drop-by-drop over a period of one hour and the resulting solution was stirred for 3 hours at 30° C., then poured into a mixture of 500 ml of 5% sulfuric acid and 200 g of ice. The ether layer was separated and the aqueous layer was extracted with ether. The ether layer and extracts were combined and the ether was evaporated. The residue was recrystallized from hot hexane, then from cold methanol, to give 4, as a solid, mp: 109°-110° C.
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