Z-Thr(tbu)-ome → (2S,3R)-Methyl 2-amino-3-(tert-butoxy)butanoate

HRID 1076407Notes

Reaction equation

HRID 1076407 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:10]([O:12][CH3:13])=[O:11])[C@@H:3]([CH3:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[H][H]>C(O)(=O)C.[Pd].C>[NH2:1][C@H:2]([C:10]([O:12][CH3:13])=[O:11])[C@@H:3]([CH3:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 2

HCID 59113197Z-Thr(tbu)-omeHCID 178418361HCID 178418361, compound

Product 1

HCID 7018834(2S,3R)-Methyl 2-amino-3-(tert-butoxy)butanoate

Reagents, catalysts & solvents 2

HCID 14818447PalladiumcarbonCatalystHCID 176Acetic AcidSolvent

Procedure

12.92 g (40mmols) of Z-Thr(tBu)-OMe are hydrogenated in 200 ml of glacial acetic acid and 3 g of Pd-charcoal (10%) at room temperature. The hydrogen uptake is finished after 1 hour. The solution is freed of the catalyst by filtration and is evaporated in a waterpump vacuum at 35°C. After drying in a high vacuum at 35°C 7.3 g of an oil result, which according to a thin layer chromatogram is a single substance and is directly further used.

Workup

  1. customat room temperature
  2. filtrationThe solution is freed of the catalyst by filtration
  3. customis evaporated in a waterpump vacuum at 35°C
  4. dry with materialAfter drying in a high vacuum at 35°C 7.3 g of an oil
  5. customresult

Sources & evidence

ORD record
ord-a926c3cb1a0d459da1056122b7103c2a
Source dataset
uspto-grants-1976_05
Patent number
US03956260

Reaction notes

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