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

HRID 2232690Notes

Reaction equation

HRID 2232690 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 0.1N HCl 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-β-benzyl-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-c0722b6b57654ba586abe8d9b838dd2b
Source dataset
uspto-grants-1988_11
Patent number
US04788332

Reaction notes

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