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

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

1. customThe mixture was transferred to an autoclave reactor
2. filtrationThe solid was filtered off
3. stirringstirred for 30 min
4. customthe completion of the reaction
5. concentrationThe reaction mixture was concentrated under reduced pressure
6. dissolutiondissolved in EtOAc
7. washwashed with NaHCO3, brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure

ORD 기록

ord-793439fe84414bd4aeb35a39a85c5e57

출처 데이터셋

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08759374B2