Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 66818343 | HCID 66818343 | — |
| Solvent | Dichloromethane methanol | HCID 21226129 | — |
| Product | HCID 66817379 | HCID 66817379 | 86% |
Reaction Steps
2-Cyclohexyl-8-{(E)-2-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-indol-5-yl]-ethenesulfonyl}-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (41.9 mg, 0.0755 mmol) was dissolved in a methylene chloride-methanol mixed solution (1:1, 1.5 ml). Trifluoroacetic acid (0.35 ml) was added and the mixture was stirred for two days. A saturated aqueous sodium bicarbonate solution and water were added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by P-TLC (ethyl acetate-methanol) to give 2-cyclohexyl-8-{(E)-2-[1-((S)-2,3-dihydroxy-propyl)-1H-indol-5-yl]-ethenesulfonyl}-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (33.4 mg, 86%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09169254B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-bddbdf9d2e1e4c6aa7ae4a7a71a074a6 |
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| Source note | uspto-grants-2015_10 |
|---|