Hydrochloric Acid → N-benzenesulfonyl-L-valyl-L-proline

HRID 1073995Notes

Reaction equation

HRID 1073995 reaction equation
C([O:8][C:9](=[O:31])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:30])[C@H:16]([CH:27]([CH3:29])[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.[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:31])=[O:8])=[O:30])[CH:27]([CH3:29])[CH3:28])(=[O:20])=[O:19])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 14858848N-benzenesulfonyl-L-valyl-L-proline benzylesterHCID 178418361HCID 178418361, compound

Product 1

HCID 14858846N-benzenesulfonyl-L-valyl-L-prolineYield 689.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

N-benzenesulfonyl-L-valyl-L-proline benzylester 200 g, 4.5 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 thus obtained was concentrated under reduced pressure. The residue thus obtained was dissolved in water (20 ml), and 1N aqueous hydrochloric acid (10 ml) was added thereto to give white crystals. They were recrystallized from methylene chloride, ethyl acetate and petroleum ether to obtain N-benzenesulfonyl-L-valyl-L-proline (yield: 1 11 g, 69.6%).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate thus obtained
  3. concentrationwas concentrated under reduced pressure
  4. customThe residue thus obtained
  5. customto give white crystals
  6. customThey were recrystallized from methylene chloride, ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-766bed5050ba452e804740dd1c90f6b1
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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