Reaction equation
O[C:2]1([CH2:16][CH2:17][NH:18][C:19](=[O:23])[O:20][CH2:21][CH3:22])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]21C[CH2:14][CH2:13][CH2:12]2.S(=O)(=O)(O)O.O.[C:30](O)(=O)C>>[N:18]1([C:19]([O:20][CH2:21][CH3:22])=[O:23])[C:17]23[CH2:30][CH2:6][CH2:7][CH2:8][C:9]2([CH2:10][CH2:11][C:2]2[CH:3]=[CH:12][CH:13]=[CH:14][C:16]=23)[CH2:4][CH2:5]1Participants
5
Procedure
A solution of the product from Example 13 (1.68 g, 5.29 mmol) in 15 mL of 3:1 acetic acid/concentrated sulfuric acid (v/v) was stirred at room temperature for 18 hours. The reaction mixture was poured into water (50 mL) and the resulting mixture was extracted with CH2Cl2 (4×30 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated. The residue was dissolved in CH2Cl2 (100 mL and washed with saturated aq. bicarbonate solution (30 mL). The organic phase was dried (MgSO4), filtered and concentrated. The residue was purified by chromatography (silica gel, 9:1 heptane/ethyl acetate) to give the title compound (0.94 g, 59%) as a white solid mp 67°-69° C.
Workup
- extractionthe resulting mixture was extracted with CH2Cl2 (4×30 mL)
- dry with materialThe combined organic extracts were dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- dissolutionThe residue was dissolved in CH2Cl2 (100 mL
- washwashed with saturated aq. bicarbonate solution (30 mL)
- dry with materialThe organic phase was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by chromatography (silica gel, 9:1 heptane/ethyl acetate)
Sources & evidence
- ORD record
- ord-cd260806412b4d5ebad6b73b7513bf0c
- Source dataset
- uspto-grants-1991_12
- Patent number
- US05070093
Linked notes
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