Diethyl Ether → HCID 852848, compound

HRID 1857044Notes

Reaction equation

HRID 1857044 reaction equation
[NH2:1][C@H:2]([CH2:10][OH:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[BH4-].[Na+].CCOCC.[OH-].[Na+].[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CO.O1CCCC1>[C:21]([NH:1][C@H:2]([CH2:10][OH:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Procedure

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.

Workup

  1. customN-benzoylphenylalaninol is synthesized
  2. customat 0° C.
  3. customfor 12 hours
  4. customat room temperature
  5. customevaporating organic solvent
  6. temperaturerefluxing for 3 hours
  7. additionadding 1 L of methylenechloride to the solution, vii)
  8. customthe reaction
  9. filtrationfiltering the reaction mixture, ix)
  10. washwashing the product with hot water three times, and x)

Sources & evidence

ORD record
ord-4fa2ef205e984d12bcbf301e83e236d5
Source dataset
uspto-grants-2000_11
Patent number
US06143900

Reaction notes

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