HCID 54198277, compound → L-Aspartyl-D-serine-(2,2,5-trimethylcyclopentyl)ester

HRID 620687Notes

Reaction equation

HRID 620687 reaction equation
[CH3:1][C:2]1([CH3:40])[CH2:6][CH2:5][CH:4]([CH3:7])[CH:3]1[O:8][C:9](=[O:39])[C@@H:10]([CH2:37][OH:38])[NH:11][C:12](=[O:36])[C@H:13]([CH:25](CC1C=CC=CC=1)[C:26](=[O:28])[OH:27])[NH:14]C(OCC1C=CC=CC=1)=O>CO.[Pd]>[CH3:40][C:2]1([CH3:1])[CH2:6][CH2:5][CH:4]([CH3:7])[CH:3]1[O:8][C:9](=[O:39])[C@@H:10]([CH2:37][OH:38])[NH:11][C:12](=[O:36])[C@H:13]([CH2:25][C:26](=[O:27])[OH:28])[NH2:14]

Participants

4

Reactant 1

HCID 54198277HCID 54198277, compound

Product 1

HCID 22839474L-Aspartyl-D-serine-(2,2,5-trimethylcyclopentyl)ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a magnetically stirred solution of 0.1 mole 2,2,5-trimethylcyclopentyl-D-serinate in 100 ml dry DMF at 0° C. under an argon atmosphere is added 1 equivalent of N-Cbz-L-aspartic acid β-benzyl ester followed by addition of 1 equivalent each of Cu(II) chloride and dicyclohexylcarbodiimide. After 18 hours the mixture is poured into 200 ml 0.1 NHCl and extracted with 300 ml ethyl acetate which is successively washed with saturated NaHCO3, H2O, and dried over MgSO4. Filtration and evaporation yields N-Cbz-β-benzyl-L-aspartyl-D-serine 2,2,5-trimethylcyclopentyl ester. 2 g N-Cbz-βbenzyl-L-aspartyl-D-serine 2,2,5-trimethylcyclopentyl ester in 50 ml dry CH3OH is hydrogenated in a Paar apparatus over 5% Pd/C. Upon completion of the reaction, the mixture is filtered through Celite and concentrated to dryness to yield the final product.

Workup

  1. customUpon completion of the reaction
  2. filtrationthe mixture is filtered through Celite
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c8f049ace0174a4cb64b34ef66a01ae2
Source dataset
uspto-grants-1989_04
Patent number
US04822635

Reaction notes

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