HuagongsheHuagongshe Chemistry Print Report · For research reference only
Citric Acid → HCID 66902631, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | HCID 15479118 | HCID 15479118 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66902631 | HCID 66902631 | 75% |
Reaction Steps
To a solution of (1S,2S,4S,5R,6R)-2-(tert-butoxycarbonyl)amino-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester (1.50 g, 4.20 mmol, U.S. Pat. No. 5,958,960), pyridine (0.365 mL, 4.62 mmol) and DMAP (0.513 g, 4.20 mmol) in dichloromethane (40 mL) under nitrogen add acetic anhydride (0.514 mL, 5.0 mmol). Stir at room temperature for 16 hours, dilute with dichloromethane, and pour into 10% aqueous citric acid solution (50 mL). Wash the organic layer with water (50 mL) and brine (50 mL). Dry over MgSO4, filter and concentrate in vacuo, to produce the title compound as a white solid (1.295 g, 75%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07964632B2 |
| Source dataset | uspto-grants-2011_06 |
| ORD ID | ord-ab6f90f2c1c84209b468ed370b2b9f3b |
| Source note | uspto-grants-2011_06 |