Hydrochloric Acid → HCID 14858858, compound

HRID 1074002Notes

Reaction equation

HRID 1074002 reaction equation
C([O:8][C:9](=[O:35])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:34])[C@H:16]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[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:35])=[O:8])=[O:34])[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:20])=[O:19])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 14858860HCID 14858860, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14858858HCID 14858858, compoundYield 70.5%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

N-benzenesulfonyl-L-phenylalanyl-L-proline benzylester (2.14 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 solution 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 ethyl acetate and petroleum ether to obtain N-benzenesulfonyl-L-phenylalanyl-L-proline (yield: 1.22 g, 69.8%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe solution was concentrated under reduced pressure
  3. customThe residue thus obtained
  4. customto give white crystals
  5. customThey were recrystallized from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-1f4d08f55cff4c88b3513ef41fe13bb7
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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