Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 70296054 | HCID 70296054 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 70128860 | HCID 70128860 | 66% |
Reaction Steps
68 mg of methyl 3-(tert-butoxycarbonyl)-4-[N-[(1RS,2RS)-2-(tert-butoxycarbonyl)-1-methyl-3-{5-(phenylcarbamoyl)-2-furyl}propyl]-N-{(E)-3-phenyl-2-propenyl}carbamoyl]-4-hydroxy-3-butenoate was dissolved in a mixture of 3 ml of tetrahydrofuran and 1 ml of water and stirred together with 1 ml of 1N aqueous sodium hydroxide at room temperature for 40 hours. The reaction solution was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [chloroform/methanol=20/1→10/1] to give 44 mg (yield: 66%) of the title compound as a pale yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06048894 |
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| Source dataset | uspto-grants-2000_04 |
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| ORD ID | ord-6f10afaa965d4c3287b8799e6a5592b5 |
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| Source note | uspto-grants-2000_04 |
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