Hydrochloric Acid → HCID 20610770, compound

HRID 434138Notes

Reaction equation

HRID 434138 reaction equation
[C:1]([N:4]1[C@@H:8]([CH3:9])[C:7](=[O:10])OC1=O)(=[O:3])[CH3:2].[C:12]1([CH3:21])[CH:17]=[CH:16][C:15]([C@@H:18]([NH2:20])[CH3:19])=[CH:14][CH:13]=1.Cl>C(OCC)(=O)C>[C:12]1([CH3:21])[CH:17]=[CH:16][C:15]([C@@H:18]([NH:20][C:7](=[O:10])[C@H:8]([CH3:9])[NH:4][C:1](=[O:3])[CH3:2])[CH3:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7015759(S)-1-(p-tolyl)ethanamineHCID 45086078HCID 45086078, compound

Product 1

HCID 20610770HCID 20610770, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(S)-3-Acetyl-4-methyl-2,5-oxazolidinedione (N-acetyl-L-alanine-NCA)(424 mg, 2.7 mmol) was dissolved in ethyl acetate (10 mL), followed by the addition of (S)-1-(p-tolyl)ethylamine (406 mg, 3 mmol) at 0° C. The resulting mixture was stirred for 30 minutes. The reaction mixture was poured into 1 N hydrochloric acid (25 mL), followed by extraction with ethyl acetate (25 mL). The organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate (25 mL) and a saturated aqueous solution of sodium chloride (25 mL), and was then dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure, and the resulting white solid was washed with hexane-ethyl acetate to afford the title compound (380 mg, 57%) as white crystals.

Workup

  1. extractionfollowed by extraction with ethyl acetate (25 mL)
  2. washThe organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate (25 mL)
  3. dry with materiala saturated aqueous solution of sodium chloride (25 mL), and was then dried over anhydrous magnesium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. washthe resulting white solid was washed with hexane-ethyl acetate

Sources & evidence

ORD record
ord-e5b1ae4ceafd475581a23e19078279e1
Source dataset
uspto-grants-2003_12
Patent number
US06670447B2

Reaction notes

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