HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → HCID 136359928, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | HCID 67216361 | HCID 67216361 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 136359928 | HCID 136359928 | 100% |
Reaction Steps
To a solution of ethyl 2-((cis)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentylidene)acetate (1.9 g, 3.85 mmol) in THF (30 mL) at 0° C. was added a solution of TBAF (11.55 mL, 11.55 mmol, 1 M in THF). After about 10 min, TBAF (7.70 mL, 7.70 mmol, 1 M in THF) was added. After about 1 h EtOAc and brine were added to the reaction mixture. After about one h the organic layer was separated, concd in vacuo and purified by flash chromatography on silica gel eluting with EtOAc to afford ethyl 2-((cis)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentylidene)acetate (1.3 g, 100%) as a mixture of diastereomers: LC/MS (Table 1, Method a) Rt=1.86-1.90 min; MS m/z: 340 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08426411B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-1df584a307f94d6d997ca7abc3583a88 |
| Source note | uspto-grants-2013_04 |