Hydrochloric Acid → HCID 14858850, compound

HRID 1073998Notes

Reaction equation

HRID 1073998 reaction equation
C([O:8][C:9](=[O:32])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:31])[C@H:16]([C@H:27]([CH2:29][CH3:30])[CH3:28])[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].Cl>CO.O.[C].[Pd].C(Cl)Cl>[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:32])=[O:8])=[O:31])[C@H:27]([CH2:29][CH3:30])[CH3:28])(=[O:20])=[O:19])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 14858852HCID 14858852, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14858850HCID 14858850, compoundYield 73.7%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

N-benzenesulfonyl-L-isoleucyl-L-proline benzylester (1.96 g, 4.3 mmole) was dissolved in methanol 40 ml ), and water (5 ml) solution of sodium bicarbonate (0.42 g, 5 mmole) was added thereto. Hydrogen gas was passed through the solution in the presence of 5% palladium-carbon as a catalyst for 3 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure and the residue thus obtained was dissolved in water (20 ml), methylene chloride (100 ml) was added thereto, and at least 1N aqueous hydrochloric acid (10 ml) was added thereto while vigorous stirring. The methylene chloride layer was taken and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue thus obtained was recrystallized from ethyl acetate and petroleum ether to give N-benzenesulfonyl-L-isoleucyl-L-proline (yield: 1.16 g, 73.7%).

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customthe residue thus obtained
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue thus obtained
  8. customwas recrystallized from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-4001bfcac2e04dd3a8cecec209ba0b4d
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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