Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl Alcohol | HCID 244 | — |
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | (2R,4R)-4-amino-5-(3'-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester | HCID 86682253 | — |
| Product | HCID 86682257 | HCID 86682257 | 101.3% |
Reaction Steps
Benzyl alcohol (13.0 mL, 126 mmol) was added to (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester (1.9 g, 5.3 mmol) followed by 4.0 M HCl in 1,4-dioxane (5.3 mL, 21.3 mmol), and the mixture was stirred at 60° C. for 1 hour. The mixture was purified (Interchim reverse phase chromatography column; 30-90% MeCN in water with 0.05% TFA) to yield (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxy-pentanoic acid benzyl ester (2.2 g) as a white solid. (evaporated in vacuo with water (4×300 mL) to remove excess benzyl alcohol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08691868B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-57317e1e0f25498ab870cdf336414401 |
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| Source note | uspto-grants-2014_04 |
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