Table 1. Optimization of Deprotection of 3 with Various Acids and Solvents.
entry | acid | solvent | time (h) | conversion (%)a |
---|---|---|---|---|
1 | TsOH (10%) | H2O | 20 | 0 |
2 | TsOH (10%) | THF-H2O | 5 | <5 |
3 | HCl (2 M) | ether-H2O | 20 | 30 |
4 | HCl (2 M) | THF-H2O | 20 | 35 |
5 | H2SO4 (2 M) | AcOH-H2O (1:1)b | 36 | 40 |
6 | AcOH (25%)c | CH2Cl2-H2O (4:1)b | 36 | <10 |
7 | TFA (2%)c | CH2Cl2-H2O (4:1)b | 36 | <10 |
8 | TFA (16%)c | CH2Cl2-H2O (4:1)b | 12 | 100 |
Conversion was measured by 1H NMR.
Volume ratio.
Volume ratio to total solvent.