Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 69736935 | HCID 69736935 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 22279655 | HCID 22279655 | 96% |
Reaction Steps
2-Methoxycarbonylamino-2-methyl-4-[4-(5-phenylpent-1-ynyl)thiophen-2-yl]butanoic acid ethylester (0.82 g, 1.92 mmol) obtained in Example 25 (g) was dissolved in a mixture of ethanol (15 ml) and tetrahydrofuran (10 ml), and lithium chloride (0.24 g, 5.75 mmol) and sodium borohydride (0.22 g, 5.75 mmol) were added thereto in an ice bath, and then the reaction mixture was stirred for 2 hours at 70° C. under a nitrogen atmosphere. After the reaction solution was acidified with 1N hydrochloride acid, the resulting solution was extracted with ethyl acetate, and the ethyl acetate layer was washed with a saturated aqueous sodium chloride solution. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=4:1-1:1) to give the title compound (0.65 g, 96% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06964976B2 |
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| Source dataset | uspto-grants-2005_11 |
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| ORD ID | ord-804cf80985d3481fad263144bf8b335e |
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| Source note | uspto-grants-2005_11 |
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