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

HRID 1580865Notes

Reaction equation

HRID 1580865 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]>C(O)(=O)C.[Pd]>[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

4

Reactant 1

HCID 59113197Z-Thr(tbu)-ome

Product 1

HCID 7018834(2S,3R)-Methyl 2-amino-3-(tert-butoxy)butanoateYield 96.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

12.92 g (40 mmols) of Z-Thr(tBu)-OMe are hydrogenated in 200 ml of glacial acetic acid and 3 g of Pd on charcoal (10 %) at room temperature. The absorption of hydrogen is complete after 1 hour. The solution is freed of the catalyst by filtration and is evaporated under 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 homogeneous and is directly used further.

Workup

  1. customat room temperature
  2. customThe absorption of hydrogen
  3. filtrationThe solution is freed of the catalyst by filtration
  4. customis evaporated under a waterpump vacuum at 35°C
  5. customAfter drying in a high vacuum at 35°C

Sources & evidence

ORD record
ord-69fd7e875c5648beb449ca80ca2b612a
Source dataset
uspto-grants-1976_01
Patent number
US03934008

Reaction notes

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