Benzyl chloroformate → (s)-Tert-butyl 1-(benzyloxycarbonylamino)-3-hydroxypropan-2-yl(methyl)carbamate

To a solution of the crude (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-yl(methyl)carbamate (1.8 g, ˜4.90 mmol) in MeOH (20 mL) was added Pd/C (300 mg). The mixture was transferred to an autoclave reactor, charged with hydrogen (45 psi), and stirred at RT overnight. The solid was filtered off. To the filtrate were added CbzCl (0.83 mL, 5.88 mmol) and DIEA (1.22 mL, 7.35 mmol) and the resulting mixture was stirred at RT for 30 min. The reaction mixture was concentrated under reduced pressure and dissolved in EtOAc. The organic mixture was washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give [(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-hydroxy-propyl]carbamic acid benzyl ester (2.2 g of crude), which was used without purification (2.2 g, crude). LRMS (M+H+-Boc) m/z 239.1.

1. customThe mixture was transferred to an autoclave reactor
2. filtrationThe solid was filtered off
3. stirringthe resulting mixture was stirred at RT for 30 min
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. dissolutiondissolved in EtOAc
6. washThe organic mixture was washed with NaHCO3 and brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-966e088796bc4d9ab4bad20d68f1b332

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895582B2