How do you deprotect the NHBoc group in the presence of the OTBS group?

30 September 2014 1 4K Report

We need a free amine from the NHBoc

Cavelier and Enjalbal (F. Cavelier and C. Enjalbal, Tetrahedron Lett., 1996, 37, 5131) reported the selective removal of N-Boc protection in the presence of either TBS or TBDPS ethers using a saturated solution of HCI in ethyl acetate, 7.5 M, 25 ºC, 8h. The choice of solvent is crucial to get high selectivity; in methanol the fully deprotected

product is obtained.

You could try also:

Removal of BOC in presence of TFA:DCM 1:3. Possible subsequent silyl deprotection with HF in MeCN at 0 ºC

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