Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Benzenesulfonyl chloride | HCID 7369 | — |
| Reactant | Benzenesulfonamide | HCID 7370 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 3-Ethoxy-2,2-dimethyl-3-oxopropanoic acid | HCID 231754 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58728741 | HCID 58728741 | — |
Reaction Steps
Benzenesulfonamide was made by adding benzenesulfonyl chloride to a solution of ammonia in tetrahydrofuran and evaporating to a solid. Benzenesulfonamide (87 mg, 0.50 mmole) was added to a shaken suspension of 3-ethoxy-2,2-dimethyl-3-oxopropanoic acid (100 mg, 0.62 mmole) reactivated on PS-DCC resin (1.62 g, 1.25 mmole) and 1.50 mmole of N,N-dimethylpyridin-4-amine in DCE. When reaction is complete the resin is filtered off and the organic layer washed with 1N HCl dried and evaporated. The resulting residue was dissolved in 6 ml of ethanol and 6 ml of 1N LiOH was added and heated to 40° C. The reaction was neutralized with 1N HCl and evaporated to afford 2,2-dimethyl-3-oxo-3-[(phenylsulfonyl)amino]propanoic acid as a crude product which was used with no further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07645771B2 |
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| Source dataset | uspto-grants-2010_01 |
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| ORD ID | ord-a4e39f4c82cf4821b6f381cf11f26100 |
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| Source note | uspto-grants-2010_01 |
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