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

HRID 971540Notes

Reaction equation

HRID 971540 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-60171766c2f9461b85f221ee39ec732e
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

Loading…