Z-L-Dap(boc)-OL → (S)-tert-Butyl (2-amino-3-hydroxypropyl)carbamate

HRID 1934685Notes

Reaction equation

HRID 1934685 reaction equation
C(OC([NH:11][C@@H:12]([CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][OH:14])=O)C1C=CC=CC=1>[Pd].CO.O1CCOCC1>[NH2:11][C@@H:12]([CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][OH:14]

Participants

5

Reactant 1

HCID 10734767Z-L-Dap(boc)-OL

Product 1

HCID 10702853(S)-tert-Butyl (2-amino-3-hydroxypropyl)carbamateYield 105.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

10% Palladium on activated carbon (10 mg) was added to a solution of (S)-2-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)propanol (920 mg) in methanol (10 mL) and dioxane (1 mL). The mixture was stirred under hydrogen atmosphere (3.5 atm) for one and a half days at ambient temperature. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate, dried over magnesium sulfate, and concentrated in vacuo to give (S)-2-amino-3-(tert-butoxycarbonylamino)propanol (571 mg) as a white solid substance.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2da21c72f9204bdcb25e706b8670a32d
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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