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

HRID 1679829Notes

Reaction equation

HRID 1679829 reaction equation
[CH3:1][C@@H:2]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C@H:3]([NH:8]C(OCC1C=CC=CC=1)=O)[C:4]([O:6][CH3:7])=[O:5]>C(O)(=O)C.[C].[Pd]>[NH2:8][C@H:3]([C:4]([O:6][CH3:7])=[O:5])[C@@H:2]([CH3:1])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21]

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 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

12.92 Grams (40 mmols) of Z-Thr-(tBu)-OMe in 200 ml of glacial acetic acid and 3 g of palladium carbon (10% Pd) are hydrogenated at room temperature. The absorption of hydrogen ceases after one hour. The catalyst is filtered off and the filtrate evaporated at 35° C. in a water-jet vacuum. The residue is dried in a high vacuum at 35° C. and yields 7.3 g of an oil which is unitary according to its thin-layer chromatogram and can be further used as it is.

Workup

  1. customare hydrogenated at room temperature
  2. customThe absorption of hydrogen ceases after one hour
  3. filtrationThe catalyst is filtered off
  4. customthe filtrate evaporated at 35° C. in a water-jet vacuum
  5. customThe residue is dried in a high vacuum at 35° C.

Sources & evidence

ORD record
ord-7223f394e67d4e9f831bd7028814d954
Source dataset
uspto-grants-1981_06
Patent number
US04271068

Reaction notes

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