HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylamine → (R)-N,N-Dimethyl-3-[(2-nitro-4-sulfamoylphenyl)amino]-4-phenylsulfanylbutanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | (r)-3-(2-Nitro-4-sulfamoylphenylamino)-4-(phenylthio)butanoic acid | HCID 11683013 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (R)-N,N-Dimethyl-3-[(2-nitro-4-sulfamoylphenyl)amino]-4-phenylsulfanylbutanamide | HCID 11553925 | — |
Reaction Steps
A solution of Example 122E (411 mg, 1 mmol), 2M dimethylamine in THF (1 mL), EDCI (296 mg, 1.5 mmol), and DMAP (10 mg) in DMF (10 mL) at room temperature was stirred for 16 hours, diluted with ethyl acetate (200 mL), washed sequentially with 1N HCl (50 mL), water (50 mL), and brine (20 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 100% ethyl acetate to provide the desired product. MS (ESI(+)) m/e 439 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06720338B2 |
| Source dataset | uspto-grants-2004_04 |
| ORD ID | ord-6f406aba480445cba8daba0f4872de50 |
| Source note | uspto-grants-2004_04 |