Ethyl Acetate → HCID 14858876, compound

HRID 1074014Notes

Reaction equation

HRID 1074014 reaction equation
C([O:8][C:9](=[O:40])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:39])[C@H:16]([CH2:27][CH:28](CC1C=CC=CC=1)[C:29](=[O:31])[OH:30])[NH:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])C1C=CC=CC=1.C(=O)(O)[O-].[Na+].[H][H].C(OCC)(=O)C>CO.[C].[Pd].O>[C:21]1([S:18]([NH:17][C@H:16]([C:15]([N:11]2[CH2:12][CH2:13][CH2:14][C@H:10]2[C:9]([OH:40])=[O:8])=[O:39])[CH2:27][CH2:28][C:29](=[O:30])[OH:31])(=[O:20])=[O:19])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 54038054HCID 54038054, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14858876HCID 14858876, compoundYield 76.9%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

N-benzenesulfonyl-γbenzyl-L-glutamyl-L-proline benzylester (2.61 g, 4.6 mmole) was dissolved in methanol (40 ml), and water (5 ml) suspension of sodium bicarbonate (0.84 g, 10 mmole) was added thereto. Hydrogen gas was passed through the solution in the presence of 5% palladium-carbon as a catalyst for 4 hours. The catalyst was removed by filtration, and the solvent was distilled off under reduced pressure, and the residue thus obtained was dissolved in water (30 ml). The mixture was washed with two 30 ml portions of diethyl ether, to the water layer 1N aqueous hydrochloric acid (15 ml) was added, and the solution thus obtained was concentrated under reduced pressure. The white residue thus obtained was dispersed in a mixture (100 ml) of ethyl acetate and methanol (1:1), and the mixture was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain white solid. It was recrystallized from methanol, ethyl acetate and petroleum ether to obtain N-benzenesulfonyl-L-glutamyl-L-proline (yield: 1.36 g, 76.5%).

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe residue thus obtained
  5. washThe mixture was washed with two 30 ml portions of diethyl ether, to the water layer 1N aqueous hydrochloric acid (15 ml)
  6. additionwas added
  7. customthe solution thus obtained
  8. concentrationwas concentrated under reduced pressure
  9. customThe white residue thus obtained
  10. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  11. distillationThe solvent was distilled off under reduced pressure
  12. customto obtain white solid
  13. customIt was recrystallized from methanol, ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-b12cc302cd2341b3a91e9728a9cfd7f2
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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