Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Dimethyl Sulfoxide | HCID 679 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86753303 | HCID 86753303 | — |
Reaction Steps
The compound resulting from Example 17A in THF is added dropwise to a -70° C. solution containing oxalyl chloride, DMSO and methylene chloride. After addition, the mixture is stirred 45 minutes at -70° C., then added dropwise, maintaining the internal temperature below -50° C., triethylamine in methylene chloride. The mixture is then warmed to 0° C. and 10% citric acid is added. The layers are separated and the organic layer is washed with 10% sodium bicarbonate and 10% sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05831115 |
|---|
| Source dataset | uspto-grants-1998_11 |
|---|
| ORD ID | ord-735794df33a348ae8f601035b6152c1d |
|---|
| Source note | uspto-grants-1998_11 |
|---|
