Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzoic Acid | HCID 243 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | HCID 66671372 | HCID 66671372 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66671286 | HCID 66671286 | 74.6% |
Reaction Steps
Benzoic acid (48.5 mg), 4-dimethylaminopyridine (24.3 mg) and triethylamine (0.08 ml) were added to a solution of tert-butyl 2-(2-{[(benzyloxy)carbonyl]amino}ethyl)-5-biphenyl-4-yl-3-hydroxypentanoate (200 mg) in dichloromethane (5 ml) at 0° C. and the reaction mixture was stirred for 15 minutes. 1-Ethyl-3-(3′-dimethylaminopropyl)-carbodiimide (152 mg) was added and the reaction mixture was stirred overnight. The reaction mixture was taken in distill water and extracted with dichloromethane (20 ml). The organic layer was washed with dilute sodium bicarbonate solution, brine solution, dried over anhydrous sodium sulphate and evaporated under vacuum. The residue thus obtained was purified by column chromatography using 10% ethyl acetate in hexane as eluent to furnish the title compound (180 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08710261B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-604810ff0bc1461e987ca625dd371fa9 |
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| Source note | uspto-grants-2014_04 |
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