Chloroform methanol → tert-Butyl L-alanyl-L-prolinate

HRID 971571Notes

Reaction equation

HRID 971571 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:4]([N:6]1[CH2:17][CH2:16][CH2:15][C@H:7]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:5])[CH3:3].[H][H].C(Cl)(Cl)Cl.CO>CO.[Pd]>[NH2:1][C@H:2]([C:4]([N:6]1[CH2:17][CH2:16][CH2:15][C@H:7]1[C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])=[O:5])[CH3:3]

Participants

6

Reactant 3

HCID 21584188Chloroform methanolHCID 54380188N-[(Phenylmethoxy)carbonyl]-L-alanyl-L-proline 1,1-dimethylethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 12939800tert-Butyl L-alanyl-L-prolinate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

9.36 g of Z-Ala-Pro-OtBu are hydrogenated in 100 ml of methanol in the presence of 500 mg of Pd on charcoal (10%) at room temperature. The hydrogen uptake has ended after 90 minutes. The solution is freed of catalyst by filtration and evaporated in a waterpump vacuum at 30° C. to give an oil. This proves to be homogeneous in a thin layer chromatogram on silica gel. Rf = 0.35 in the system chloroform-methanol (1:1).

Workup

  1. filtrationThe solution is freed of catalyst by filtration
  2. customevaporated in a waterpump vacuum at 30° C.
  3. customto give an oil

Sources & evidence

ORD record
ord-c966853c63414d8b80bb1ed41d4e39ca
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

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