HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,2,2-Trifluoroethanol → HCID 58438631, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,2,2-Trifluoroethanol | HCID 6409 | — |
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | (2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acid | HCID 7005057 | — |
| Reactant | (R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acid | HCID 7146275 | — |
| Reactant | Oxalic acid--2-oxa-6-azaspiro(3.3)heptane (1/1) | HCID 53308464 | — |
| Reactant | 2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid | HCID 57829653 | — |
| Reactant | 2-(1-methyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid | HCID 67008937 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 58438631 | HCID 58438631 | — |
Reaction Steps
Prepared according to the procedure outlined in Example 1 substituting 2-oxa-6-aza-spiro[3.3]heptane oxalate for pyrrolidine, Boc-D-cyclopropyl glycine for Boc-D-tert-leucine, and 2-(1-methyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid for 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid. N-Boc deprotection in step 2 was achieved using 2,2,2-trifluoroethanol in a microwave reactor. SEM deprotection in step 4 was achieved using CsF in refluxing acetonitrile. MS: (M+H)+=422.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08518945B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-af6e846db40b4ec2b4e13dea8d1d6841 |
| Source note | uspto-grants-2013_08 |