Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate | HCID 57717474 | — |
| Reactant | 7-(3-(Phenyl)phenylcarbamoyl)heptanoic acid | HCID 58756823 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Thionyl Chloride | HCID 24386 | — |
| Product | HCID 59737195 | HCID 59737195 | 69.7% |
Reaction Steps
Acid 183 (0.103 g, 0.32 mmol) in thionyl chloride (3 mL) with a few drops of DMF was stirred at room temperature for 15 min then concentrated, diluted with dry THF (10 mL), cooled to 0° C. then treated with amine 4 (0.12 g, 0.41 mmol) and triethylamine (0.086 mL, 0.61 mmol). The reaction mixture was stirred at 0° C. for 30 min then quenched with aqueous NH4Cl, extracted with AcOEt, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (eluent: 50% AcOEt-hexane) to give the title compound 184 (0.111 g, 52% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08598168B2 |
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| Source dataset | uspto-grants-2013_12 |
|---|
| ORD ID | ord-241631d01e57491fb4649b8b3f889573 |
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| Source note | uspto-grants-2013_12 |
|---|
