Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | Ethyl N-(cyanomethyl)-N-(3,4-dichlorophenyl)glycinate | HCID 57488845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Product | HCID 57418651 | HCID 57418651 | 96.6% |
Reaction Steps
Ethyl N-(cyanomethyl)-N-(3,4-dichlorophenyl)glycinate (1.00 g, 3.48 mmol) was dissolved in 10 mL of THF and treated with LiOH (83.4 mg, 3.48 mmol) dissolved in 2 mL of water. After 2 h, HPLC (Eclipse XDB-C18, 4.6×250 mm, 5 micron, 1-99% CH3CN/H2O with 0.1% trifluoroacetic acid) showed that all of the starting material (Rt=7.6 min) was gone and that a single new peak (Rt=6.2 min) had formed. The reaction mixture was treated with a solution of 4.0M HCl in dioxane (1.74 mL, 6.96 mmol) and then the solvent was removed by rotary evaporation followed by high vacuum to give 870 mg (3.36 mmol, 96%) of N-(cyanomethyl)-N-(3,4-dichlorophenyl)glycine as a white solid which was used in subsequent chemistry without further purification. LC/MS (APCI) m/e 232 [M−CN]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07432258B2 |
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| Source dataset | uspto-grants-2008_10 |
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| ORD ID | ord-84f2b5c5c37e4b1ea5ced3dc84ad4176 |
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| Source note | uspto-grants-2008_10 |
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