HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Methyl 3-[N-(p-chlorobenzyl)-5-allyloxy-3-(t-butylthio)indol-2-yl]-2,2-dimethylpropanoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Allyl bromide | HCID 7841 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-hydroxy-1H-indol-2-yl)-2,2-dimethylpropanoate | HCID 14980577 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Methyl 3-[N-(p-chlorobenzyl)-5-allyloxy-3-(t-butylthio)indol-2-yl]-2,2-dimethylpropanoic acid | HCID 19734346 | — |
Reaction Steps
500 mg. of methyl 3-[N-(p-chlorobenzyl)-5-hydroxy-3-(t-butylthio)indol-2-yl]-2,2-dimethylpropanoate from Step C of Example 1 was dissolved in 5 mL of DMF and 20 mg of K2CO3 and 150 mg of allyl bromide were added. The reaction was stirred for 16 hrs. Water was added and the organic phase extracted with EtOAc (3×5 mL). The organic phase was dried with MgSO4 and evaporated to yield, after chromatography on silica gel (EtOAc:hexane 1:5), the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05272145 |
| Source dataset | uspto-grants-1993_12 |
| ORD ID | ord-4c1ffa06c75c43bb9f9ed5faff454cda |
| Source note | uspto-grants-1993_12 |