Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 66705951 | HCID 66705951 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 66705917 | HCID 66705917 | 84% |
Reaction Steps
To a solution of (S)-4-{2-[4-(4-chloro-benzoylamino)-phenyl]-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (438 mg) in acetonitrile (5 ml) were added water (4 ml) and trifluoroacetic acid (0.29 ml). The mixture was heated at 80° C. for 4.5 h. The mixture was then cooled to room temperature and poured into 1 M aq. NaOH and extracted twice with EtOAc/THF. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford N-[4-((S)-3-amino-4-hydroxy-butyl)-phenyl]-4-chloro-benzamide (255 mg, 84%) a white solid. MS (ISP): 321.2 ([{37Cl}M+H]+), 319.2 ([{35Cl}M+H]).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09132136B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-49388cdf7cf64b42a7069f906b6deaa7 |
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| Source note | uspto-grants-2015_09 |
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