Hydrochloric Acid → HCID 14858870, compound

HRID 1074012Notes

Reaction equation

HRID 1074012 reaction equation
C([O:8][C:9](=[O:30])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:29])[C@H:16]([CH2:27][OH: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(OCC)(=O)C>[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:30])=[O:8])=[O:29])[CH2:27][OH:28])(=[O:19])=[O:20])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 14858872HCID 14858872, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14858870HCID 14858870, compoundYield 85%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

N-benzenesulfonyl-L-seryl-L-proline benzylester (1.96 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 solvent was distilled off under reduced pressure. The residue thus obtained was dissolved in water (20 ml) and 1N aqueous hydrochloric acid (10 ml) was added thereto. The solution was concentrated under reduced pressure to produce solid material, which is a white residue. The residue was dispersed in ethyl acetate (100 ml) and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a white solid. It was recrystallized from ethyl acetate and petroleum to obtain N-benzenesulfonyl-L-seryl-L-proline (yield: 1.31 g, 66.9%).

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue thus obtained
  4. concentrationThe solution was concentrated under reduced pressure
  5. customto produce solid material, which
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customto obtain a white solid
  9. customIt was recrystallized from ethyl acetate and petroleum

Sources & evidence

ORD record
ord-636104c63c0b4c549d6ac293afc9a8e2
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

Loading…