Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Benzoyl chloride | HCID 7412 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | phenylalaninol, (S)- | HCID 447213 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 852848 | HCID 852848 | 81.1% |
Reaction Steps
N-benzoylphenylalaninol is synthesized by following steps of: i) suspending 1 mole (163 g) of L-phenylalaninol to 1 L of tetrahydrofuran, ii) adding 2.5 mole (100 g) of NaBH4 to the solution, iii) dropping 1.25 mole of ether-diluted sulfuric acid (66 ml, total volume 200 ml) to the solution at 0° C., iv) after reacting the solution for 12 hours at room temperature, adding 200 ml of methanol slowly, v) after adding 1 L of 5N-NaOH, evaporating organic solvent and refluxing for 3 hours, vi) after cooling to room temperature, adding 1 L of methylenechloride to the solution, vii) adding 1 mole of benzoylchloride to the solution slowly at 0° C., viii) after finishing the reaction, filtering the reaction mixture, ix) washing the product with hot water three times, and x) obtaining 207 g (81%) of N-benzoylphenylalaninol after drying the product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06143900 |
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| Source dataset | uspto-grants-2000_11 |
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| ORD ID | ord-4fa2ef205e984d12bcbf301e83e236d5 |
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| Source note | uspto-grants-2000_11 |
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