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. 2014 Sep 25;79(20):9546–9555. doi: 10.1021/jo5016135

Table 1. Optimization of Deprotection of 3 with Various Acids and Solvents.

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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
a

Conversion was measured by 1H NMR.

b

Volume ratio.

c

Volume ratio to total solvent.