HCID 14858892, compound → HCID 14858894, compound

HRID 1074019Notes

Reaction equation

HRID 1074019 reaction equation
C([O:8][C:9](=[O:46])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:45])[C@H:16]([CH2:30][CH2:31][CH2:32][CH2:33][NH:34]C(OCC1C=CC=CC=1)=O)[NH:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-])=O)(=[O:20])=[O:19])C1C=CC=CC=1.[H][H]>CO.[C].[Pd].O>[NH2:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[S:18]([NH:17][C@H:16]([C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([OH:46])=[O:8])=[O:45])[CH2:30][CH2:31][CH2:32][CH2:33][NH2:34])(=[O:20])=[O:19]

Participants

6

Reactant 2

HCID 14858892HCID 14858892, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14858894HCID 14858894, compoundYield 91.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Nα -o-nitrobenzenesulfonyl-Nε -benzyloxycarbonyl-L-lysyl-L-proline benzylester (5.82 g, 8.9 mmole) was dissolved in methanol (40 ml), and hydrogen gas was Passed through the solution in the presence of 5% palladium-carbon as a catalyst for 6 hours. The catalyst was removed by filtration, and the solvent was distilled off under reduced pressure. The residue thus obtained was dissolved in water (25 ml). The solution was washed with three 25 ml portions of diethyl ether and the water layer as separated was freeze-dried to obtain Nα -o-aminobenzenesulfonyl-L-lysyl-L-proline (yield: 3.23 g, 90.9%).

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue thus obtained
  4. washThe solution was washed with three 25 ml portions of diethyl ether
  5. customthe water layer as separated
  6. customwas freeze-dried

Sources & evidence

ORD record
ord-1675a79fde994e6b931873d956df3835
Source dataset
uspto-grants-1990_11
Patent number
US04971993

Reaction notes

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