[H-].[Na+].C[C:4](OS(C1C=CC(C)=CC=1)(=O)=O)([CH2:21][CH2:22][CH3:23])[CH2:5][C:6]1[C:15]([NH:16][C:17](=[O:19])[CH3:18])=[CH:14][CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]=1[OH:20].O.[CH2:36]1COCC1>C(OCC)(=O)C>[CH3:36][C:22]1([CH3:23])[CH2:21][CH2:4][CH2:5][C:6]2[C:15]([NH:16][C:17](=[O:19])[CH3:18])=[CH:14][CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]=2[O:20]1To a mixture of 2.2 g sodium hydride (60%) and 20 ml THF is added dropwise at 0° C. a solution of 15 g of methyl 3-(2'-methyl-2'-tosyloxypentyl)-4-acetylaminosalicylate in 10 ml THF. This is allowed to come to room temperature over several hours, then chilled and 2 ml H2O added slowly. This is then diluted with ethyl acetate, the salts filtered off, washed with water and brine, dried and concentrated to dryness to obtain methyl 2,2-dimethyl-6-acetylamino-2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylate which is used directly in the next step.
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