Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole, ammonium salt | HCID 22033809 | — |
| Reactant | HCID 67118530 | HCID 67118530 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67118826 | HCID 67118826 | 82% |
Reaction Steps
A mixture of (2-{7-(2-{[di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl)acetic acid (320 mg), 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide hydrochloride (165 mg), 1-hydroxybenzotriazole ammonium salt (131 mg) and N,N-dimethylformamide (8 mL) was stirred at room temperature for 18 hr. Water was added to the reaction solution, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtrated, and concentrated under reduced pressure. The obtained crude product was subjected to basic silica gel column chromatography (ethyl acetate:hexane=30:70 to 100:0, volume ratio) to give the title compound (262 mg, yield 55%) as an orange oil. MS 742 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08673942B2 |
|---|
| Source dataset | uspto-grants-2014_03 |
|---|
| ORD ID | ord-be1abaee100d4de48b23d382cc3048f3 |
|---|
| Source note | uspto-grants-2014_03 |
|---|