Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methanesulfonamide | HCID 72879 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 69102595 | HCID 69102595 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69537261 | HCID 69537261 | 6.7% |
Reaction Steps
To a solution of 4′-[2-[(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-(isopropylthio)-4-biphenycarboxylic acid (131 mg) in N,N-dimethylformamide (2.6 ml) were added methanesulfonamide (24.9 mg), 4-(dimethylamino)pyridine (43.7 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (91.4 mg) at room temperature and the mixture was stirred at the same temperature for 72 hours. The mixture was poured into aqueous hydrochloric acid solution (0.3N) and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/3) to give tert-butyl [(2R)-2-hydroxy-2-phenylethyl](2-[3′-(isopropylthio)-4′-[[(methylsulfonyl)amino]carbonyl]-4-biphenylyl]ethyl]-carbamate (10 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07417060B2 |
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| Source dataset | uspto-grants-2008_08 |
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| ORD ID | ord-8748cde452e24f20b38d7a6560f4c365 |
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| Source note | uspto-grants-2008_08 |
|---|