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

HRID 340993Notes

Reaction equation

HRID 340993 reaction equation
[N:1]([CH2:4][C@H:5]([N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:6][O:7]CC1C=CC=CC=1)=[N+]=[N-].[H][H].[C:26](Cl)([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27].CCN(C(C)C)C(C)C>CO.[Pd]>[CH2:29]([O:28][C:26](=[O:27])[NH:1][CH2:4][C@H:5]([N:15]([C:16]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:22])[CH3:23])[CH2:6][OH:7])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 57947389HCID 57947389, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57947595(s)-Tert-butyl 1-(benzyloxycarbonylamino)-3-hydroxypropan-2-yl(methyl)carbamateYield 132.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-966e088796bc4d9ab4bad20d68f1b332
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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