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

HRID 1074008
Notes
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Reaction equation

HRID 1074008 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]1[CH2:20][CH2:19][CH2:18][N:17]1[S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])=[O:22])C1C=CC=CC=1.C(=O)(O)[O-].[Na+].[H][H].Cl>CO.[C].[Pd].O>[C:24]1([S:21]([N:17]2[CH2:18][CH2:19][CH2:20][C@H:16]2[C:15]([N:11]2[CH2:12][CH2:13][CH2:14][C@H:10]2[C:9]([OH:31])=[O:8])=[O:30])(=[O:23])=[O:22])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 14858868N-benzenesulfonyl-L-prolyl-L-proline benzylesterHCID 178418361HCID 178418361, compound

Product 1

HCID 14858866N-benzenesulfonyl-L-prolyl-L-prolineYield 62.5%

Reagents, catalysts & solvents 3

HCID 178418390
HCID 178418390, compound
Catalyst
HCID 887MethanolSolvent
HCID 962WaterSolvent2×

Procedure

N-benzenesulfonyl-L-prolyl-L-proline benzylester (2.17 g, 4.9 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, and the residue thus obtained was dissolved in water (10 ml). 1N aqueous hydrochloric acid (10 ml) was added to the solution. The white crystals thus obtained were recrystallized from N,N-dimethylformamide, ethyl acetate and petroleum ether to obtain N-benzenesulfonyl-L-prolyl-L-proline (yield 1.08 g, 62.5%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe solution was concentrated under reduced pressure
  3. customthe residue thus obtained
  4. customThe white crystals thus obtained
  5. customwere recrystallized from N,N-dimethylformamide, ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-082c48a057b74e87bcf51edf4bed9100
Source dataset
uspto-grants-1990_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04971993

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes