C(OCC(C)C[N:8]1[CH2:11][C@H:10]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[C:9]1=[O:23])(=O)C.C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+].Cl>CO.O>[O:23]=[C:9]1[C@@H:10]([NH:12][C:13](=[O:14])[O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:11][NH:8]1
A solution of 3.12 g of 1-[(acetyloxy)-2-methyl(propyl)]-2-oxo-(3S)-[[(phenylmethoxy)-carbonyl]amino]azetidine in 70 ml of methanol and 7 ml of water was cooled to -15° C. and 1.33 g of potassium carbonate and 349 mg of sodium borohydride was added. The reaction mixture was stirred at -15° C. -0° C. After the reaction was complete (about 2 hours), the mixture was neutralized to pH 7 with 2N HCl and concentrated in vacuo. The concentrate was adjusted to pH 5.8, saturated with salt and extracted with ethyl acetate (3 times). The organic layer was dried and evaporated in vacuo. The residue was combined with material from a similar experiment and triturated with ether to give 3.30 g of the title compound.
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