HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → (1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | (1R,2R,5R)-tert-butyl 5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxylate | HCID 58282736 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxylic acid | HCID 58282725 | 48% |
Reaction Steps
To a solution of compound 39 (1.07 mmol) in anhydrous DCM (70 mL) was added TFA (42.6 mmol) slowly. The reaction mixture was stirred at room temperature for 16 hrs. The reaction mixture was concentrated and purified by silica gel chromatography (DCM/MeOH) to yield compound 40 as a yellow oil in 48% yield. MS (ESI, EI+): m/z=522 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09284307B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-96056136ac7a407cb903af1fadabd026 |
| Source note | uspto-grants-2016_03 |