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

HRID 409777Notes

Reaction equation

HRID 409777 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]([NH:1][CH2:4][C@H:5]([N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:6][OH:7])=[O:27])[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 (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.

Workup

  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

Sources & evidence

ORD record
ord-793439fe84414bd4aeb35a39a85c5e57
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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