HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylcarbodiimide → (2-(1Azabicyclo[2.2.2]oct-3yl)acetoxy}-2,3,5,6-tetrafluorobenzoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylcarbodiimide | HCID 12734 | — |
| Reactant | Tetrafluoro-4-hydroxybenzoic acid | HCID 98835 | — |
| Reactant | 2-(Quinuclidin-3-yl)acetic acid hydrochloride | HCID 23024147 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (2-(1Azabicyclo[2.2.2]oct-3yl)acetoxy}-2,3,5,6-tetrafluorobenzoic acid | HCID 17979834 | 235.9% |
Reaction Steps
2 g of the polymeric support resin from Example 8A (loading about 1.36 mmol/g, 2.72 mmol) are suspended in 20 ml of DMF and shaken with 1.23 g (5.98 mmol) of 1-azabicyclo[2.2.2]oct-3-ylacetic acid hydrochloride and 130 mg (1.09 mmol) of DMAP for 10 min. Then 1.06 ml (6.80 mmol) of N,N′-diisopropylcarbodiimide are added, and the mixture is shaken overnight. The resin is filtered off with suction, washed twice each with 20 ml each of DMF, THF and DCM and dried under high vacuum. 2.318 g of the polymer-bound title compound are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09433614B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-6992c5cb27204b3e83ffb979c478ad2b |
| Source note | uspto-grants-2016_09 |