Reaction #1747890

Reaction equation

111

3-(N-Cbz-N,O-Dimethyltyrosyl)amino-2-tert-butoxycarbonylamino-1-(tert-butyl-dimethylsilanyloxy)butane

→

112

Yield 90.0%

3-(N-Cbz-N,O-Dimethyltyrosyl)amino-2-tert-butoxycarbonylamino-1-butanol

Yield 90.0%

Solvents

AcOH

Conditions

Workup

1. 1
   ConcentrationThe reaction was concentrated

Procedure

A solution of 111 (15 mg, 0.086 mmol) in AcOH (1 mL) was stirred 15 h. at room temperature. The reaction was concentrated to yield 112 (11 mg, 90%) as a colorless oil. The crude residue was used with further purification in the next step. 1H-NMR (500 MHz, CDCl3): 1.04 (d, J=6.9 Hz, 3H), 1.45 (s, 9H), 2.81 (s, 3H), 2.88-2.92 (m, 1H), 3.02-3.09 (m, 1H), 3.29-3.33 (m, 1H), 3.51-3.62 (m, 1H), 3.70-3.79 (m, 1H), 3.78 (s, 3H), 4.02-4.08 (m, 1H), 4.43-4.47 (m, 1H), 4.51-4.55 (m, 1H), 5.05-5.18 (m, 2H), 5.22 (s, 2H), 5.98-5.99 (m, 1H), 6.72 ((d, J=7.9 Hz, 2H), 6.90-7.01 (m, 2H), 7.22-7.38 (m, 5H).

Source