Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 67966844 | HCID 67966844 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 57410105 | HCID 57410105 | 134.6% |
Reaction Steps
A solution of N1-[4-(1,3-dihydro-2-benzofuran-4-yloxy)phenyl]-D-alaninamide (Intermediate 7, 80 mg) and TEA (0.187 ml, 1.341 mmol) in dichloromethane (10 ml) was stirred under argon at 0° C. Triphosgene (39.8 mg, 0.134 mmol) in dichloromethane (4 ml) was added and the mixture was left under stirring at 0° C. for 45 minutes. An aqueous saturated solution of NaHCO3 was then added. The phases were separated and the aqueous one was extracted 3 times with dichloromethane. The gathered organic phases were dried over sodium sulphate and concentrated under vacuum. The crude was purified by flash chromatography (FlashMasterPersonal), using as eluents a gradient Cyclohexane/Ethyl acetate from 100:0 to 40:60. This afforded the title compound as a white solid (58.5 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09346790B2 |
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| Source dataset | uspto-grants-2016_05 |
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| ORD ID | ord-c57f0a732b3b4a2f8bd2ac74dce629a1 |
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| Source note | uspto-grants-2016_05 |
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