FMOC-TYR-OME

General procedure: Method A-using a planetary ball mill: The tritylated compound(1 mmol; typically 563 mg for 4) and In(OTf)3 (141 mg, 0.25 mmol)were allowed to mix in a stainless steel (SS) jar (capacity, 50 mL)containing SS balls (10 numbers, 10 mm o.d.) for 3.5 h (TLC, EtOAc:Hex, 1:1 for 4) in a planetary ball mill (PM-100) at550 rpm. EtOAc was added to the reaction mixture and the solutionwas transferred to a separatory funnel (50 ml 3). It was thenwashed successively with aq Na2CO3 solution (10percent, w/v, 50 ml 2)and water (50 ml), dried (Na2SO4), and concentrated underreduced pressure to afford the respective crude de-O-tritylated product. The crude product was purified by flash chromatography to free it from the by-product, TrOH (yield, 305 mg, 95.2percent, for 5from 4). It was crystallized from diethyl ether-n-Hex to obtain analytically pure product. The spectral data were in accordance with the expected structure and in agreement with the literature values. Method B—using a vibratory ball mill: The tritylated compound(1 mmol; typically 563 mg for 4) and In(OTf)3 (141 mg, 0.25 mmol)were allowed to mix in a SS jar (capacity, 10 mL) containing SSballs (20 numbers, 3 mm o.d.) for 15 min (TLC, EtOAc/Hex, 1:1 inthe case of 4) in a vibratory ball mill (MM-400) at 30 Hz. Theworkup and isolation of the product were carried out as describedin Method A above. Yield, 308 mg, 96.2percent for 5 from 4.

Molecular Weight:417.5
XLogP3:4.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:8
Exact Mass:417.15762283
Monoisotopic Mass:417.15762283
Topological Polar Surface Area:84.9
Heavy Atom Count:31
Complexity:595
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes