HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → (3R,5S)-1-pyrimidin-2-yl-5-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-3-thiol trifluoro-acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Silane, tris(1-methylethyl)- | HCID 138754 | — |
| Reactant | (2S,4R)-2-[2-(2,4,5-Trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-pyrimidine | HCID 70035536 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (3R,5S)-1-pyrimidin-2-yl-5-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-3-thiol trifluoro-acetate | HCID 9956301 | 80% |
Reaction Steps
A solution of 1.7 g (2.84 mmol) (2S,4R)-2-[2-(2,4,5-Trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-pyrimidine in 30 ml CH2Cl2 was treated at 0° C. with 8 ml TFA and 5.82 ml (28 mmol) triisopropylsilane. After 30 min at RT the solution was completely evaporated and the compound precipitated twice from Et2O/pentane to give 1.06 g (80%) (3R,5S)-1-pyrimidin-2-yl-5-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-3-thiol trifluoro-acetate (1:1) as colourless oil, MS: 356 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06660738B2 |
| Source dataset | uspto-grants-2003_12 |
| ORD ID | ord-0d29215d6e7648f4a73a2c08bf5003b6 |
| Source note | uspto-grants-2003_12 |