Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 14858852 | HCID 14858852 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Catalyst | HCID 178418390 | HCID 178418390 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 14858850 | HCID 14858850 | 73.7% |
Reaction Steps
N-benzenesulfonyl-L-isoleucyl-L-proline benzylester (1.96 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 filtrate was concentrated under reduced pressure and the residue thus obtained was dissolved in water (20 ml), methylene chloride (100 ml) was added thereto, and at least 1N aqueous hydrochloric acid (10 ml) was added thereto while vigorous stirring. The methylene chloride layer was taken and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue thus obtained was recrystallized from ethyl acetate and petroleum ether to give N-benzenesulfonyl-L-isoleucyl-L-proline (yield: 1.16 g, 73.7%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04971993 |
|---|
| Source dataset | uspto-grants-1990_11 |
|---|
| ORD ID | ord-4001bfcac2e04dd3a8cecec209ba0b4d |
|---|
| Source note | uspto-grants-1990_11 |
|---|