HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Amino-2-thioxoethyl 2,2-dimethylpropanoate → 1-(cyclohexyl)methyl-7-methoxy-3-{2-[(tertbutylcarbonyloxy)methyl]thiazol-4-yl}-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Amino-2-thioxoethyl 2,2-dimethylpropanoate | HCID 2782113 | — |
| Reactant | 2-Chloro-1-[1-(cyclohexyl)methyl-7-methoxy-1H-indol-3-yl]ethanone | HCID 86073279 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 1-(cyclohexyl)methyl-7-methoxy-3-{2-[(tertbutylcarbonyloxy)methyl]thiazol-4-yl}-1H-indole | HCID 68698760 | 99.7% |
Reaction Steps
2-Chloro-1-[1-(cyclohexyl)methyl-7-methoxy-1H-indol-3-yl]ethanone (0.73 g, 2.30 mmol) and 2-(tert-butylcarbonyloxy)thioacetamide (1.21 g, 6.89 mmol) were suspended in ethanol (10 ml) and the resulting mixture subjected to microwave irradiation at 150° C. for 10 min using an Emrys™ Optimizer EXP. The reaction mixture was concentrated in vacuo and the residue obtained was purified by flash column chromatography eluting with 5% (v/v) ethyl acetate in n-heptane to afford 1-(cyclohexyl)methyl-7-methoxy-3-{2-[(tertbutylcarbonyloxy)methyl]thiazol-4-yl}-1H-indole as a yellow oil (1.01 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07700634B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-c3f0251913df425da83855f20c89a5c2 |
| Source note | uspto-grants-2010_04 |