반응 #2299622

반응 방정식

compound 108

2-(N′-tert-Butoxycarbonyl-hydrazino)-3-(3,4-dihydroxy-phenyl)-2-methyl-propionic acid methyl ester

bromophthalide

→

114

수율 32.2%

2-Hydrazino-3-[4-hydroxy-3-(3-oxo-1,3-dihydro-isobenzofuran-1-yloxy)-phenyl]-2-methyl-propionic acid methyl ester

수율 32.2%

용매

acetone

반응 조건

후처리

1. 1
   기타After removing the solvent under reduced pressure
2. 2
   기타the residue was partitioned between 10% citric acid and ethyl acetate
3. 3
   기타The organic phase was separated
4. 4
   건조dried over MgSO4
5. 5
   기타After removing the solvent under reduced pressure
6. 6
   workup.ADDITIONthe resulting residue was treated with 50% trifluoroacetic acid in dichloromethane at room temperature for 30 min
7. 7
   기타After removing the solvent
8. 8
   기타the resulting residue was purified by reverse phase preparative HPLC

실험 절차

A mixture of compound 108 (380 mg, 1.1 mmol), bromophthalide (213 mg, 1 mmol) and CsHCO3 (325 mg, 1 mmol) in acetone was stirred at room temperature for 16 h. After removing the solvent under reduced pressure, the residue was partitioned between 10% citric acid and ethyl acetate. The organic phase was separated and dried over MgSO4. After removing the solvent under reduced pressure, the resulting residue was treated with 50% trifluoroacetic acid in dichloromethane at room temperature for 30 min. After removing the solvent, the resulting residue was purified by reverse phase preparative HPLC to afford two separated stereoisomers 113 (123 mg) and 114 (120 mg), respectively. Compound 113: 1H NMR (CD3OD, 400 MHz): 1.43 (s, 3H), 2.98 (dd, 2H), 3.80 (s, 3H), 6.62–7.20 (m, 4H), 7.66–7.95 (m, 4H). MS (ESI) m/z 373.25 (M+H+) and Compound 114:1H NMR (CD3OD, 400 MHz): 1.44 (s, 3H), 2.99 (dd, 2H), 3.84 (s, 3H), 6.80–7.18 (m, 4H), 7.69–7.93 (m, 4H). MS (ESI) m/z 373.25 (M+H+).

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