HuagongsheHuagongshe Chemistry Print Report · For research reference only
Imidazole → HCID 68806846, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | 2-Dimethylaminopyridine | HCID 21885 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | N-Boc-cis-4-hydroxy-D-proline | HCID 688616 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68806846 | HCID 68806846 | — |
Reaction Steps
(2R,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (16 g, 69 mmol) was dissolved in 100 mL DMF, added imidazole (12 g, 173 mmol), dimethylaminopyridine (0.85 g, 6.9 mmol), and tert-butyldimethylsilyl chloride (12.5 g, 83 mmol). Stirred at ambient temperature overnight, dissolved in 350 mL EtOAc, washed with 10% citric acid (3×200 mL), water (2×200 mL), brine, dried with MgSO4, filtered, and concentrated to yield title compound. (20 g, 84%) APCI (AP−): 344.2 (M−H)−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07407972B2 |
| Source dataset | uspto-grants-2008_08 |
| ORD ID | ord-8e8acc00595b46408faeac4e7bde67ba |
| Source note | uspto-grants-2008_08 |