HuagongsheHuagongshe Chemistry Print Report · For research reference only
Thiocyanic acid, chloromethyl ester → [4-[(5S)-5-(acetamidomethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl]sulfanylmethyl thiocyanate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Thiocyanic acid, chloromethyl ester | HCID 76755 | — |
| Reactant | 5-(S)-Acetamidomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]oxazolidine-2-one | HCID 22966197 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | [4-[(5S)-5-(acetamidomethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl]sulfanylmethyl thiocyanate | HCID 485766 | — |
Reaction Steps
Prepared according to Method B of the General Procedures for Preparation of 5-(S)-(N-Acylaminomethyl)-3-[4′-(substituted)thio-3′-fluorophenyl]oxazolidine-2-ones from 5-(S)-acetamidomethyl-3-[4′-(triphenylmethyl)thio-3′-fluorophenyl]oxazolidine-2-one with chloromethyl thiocyanate (0.041 g, 0.38 mmol) in N-methylpyrrolidine-2-one (1 mL). The synthesis was performed at r.t. for 2 h. The crude product was purified by TLC (eluent: 10% methanol in dichloromethane). Yield 0.022 g (35%). MS (m/z): 324 [M+H]+. 1H NMR.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06531470B1 |
| Source dataset | uspto-grants-2003_03 |
| ORD ID | ord-6d4f719b0e3545e685d512010e902003 |
| Source note | uspto-grants-2003_03 |