Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Ethyl ketone | HCID 7288 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 86033134 | HCID 86033134 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 85432458 | HCID 85432458 | — |
Reaction Steps
A mixture of pentan-3-one (0.3 mmol), 2-Amino-pentanoic acid [5-(1,1-dimethyl-butyl)-[1,3,4]thiadiazol-2-yl]-amide (0.3 mmol), sodium triacetoxy borohydride (0.3 mmol) and acetic acid (0.3 mmol) in 1.0 mL of anhydrous dichloromethane and 1 ml DMF was stirred at room temperature (rt) overnight. The reaction was not complete. The mixture was treated with NaBH3CN (40 mg) and heated at 45° C. for 4 hr. All starting material was consumed. The crude solution was diluted with dilute NaOH and extracted with methylene chloride. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude products were purified through Shimadzu HPLC to give 2-(1-Ethyl-propylamino)-pentanoic acid [5-(1,1-dimethyl-butyl)-[1,3,4]thiadiazol-2-yl]-amide. LC-MS (retention time, M+1): 1.70 min, 355.3 [M+1]
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07232820B2 |
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| Source dataset | uspto-grants-2007_06 |
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| ORD ID | ord-2a4fed598a904889a63273a02704b9e2 |
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| Source note | uspto-grants-2007_06 |
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