HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → Acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | Methyl 2-((tert-butoxycarbonyl)amino)-2-hydroxyacetate | HCID 11106496 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester | HCID 10922855 | 98% |
Reaction Steps
To a solution of the product of Example 1 (10.0 g, 48.8 mmol), pyridine (7.71 g, 97.6 mmol) and DMAP (300 mg, 2.5 mmol) in THF (50 ML) was added acetic anhydride (5.47 g, 53.6 mmol) slowly at room temperature. After stirring at ambient temperature for 3 hours, the reaction was diluted with EtOAc and washed successively with 1N NaHSO4 and sat'd NaHCO3. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure affording 11.8 g (98%) of product as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05665598 |
| Source dataset | uspto-grants-1997_09 |
| ORD ID | ord-e4489cea09c34ad0913b3eaff51869af |
| Source note | uspto-grants-1997_09 |