Hydrochloric Acid → HCID 11255354, compound

HRID 434134Notes

Reaction equation

HRID 434134 reaction equation
[C:1]([N:9]1[C@@H:13]([CH3:14])[C:12](=[O:15])OC1=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C@@H:23]([NH2:25])[CH3:24])=[CH:19][CH:18]=1.CN1CCOCC1.Cl>C(OCC)(=O)C>[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C@@H:23]([NH:25][C:12](=[O:15])[C@H:13]([CH3:14])[NH:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH3:24])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 7015759(S)-1-(p-tolyl)ethanamineHCID 9855930(S)-3-benzoyl-4-methyl-2,5-oxazolidinedione

Product 1

HCID 11255354HCID 11255354, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

(S)-3-Benzoyl-4-methyl-2,5-oxazolidinedione (N-benzoyl-L-alanine-NCA) (110 mg, 0.50 mmol) was dissolved in ethyl acetate (2.5 mL), followed by the addition of a solution of (S)-1-(p-tolyl)ethylamine (68 mg, 0.50 mmol) in ethyl acetate (2.5 mL) at 0° C. A solution of N-methylmorpholine (61 mg, 0.6 mmol) in ethyl acetate (3.0 mL) was then added, followed by stirring for 30 minutes. The reaction mixture was poured into 1 N hydrochloric acid (10 mL), followed by extraction with ethyl acetate (10 mL). The organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate (10 mL) and a saturated aqueous solution of sodium chloride (10 mL), and was then dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure to afford the title compound (149 mg, 97%) as white crystals.

Workup

  1. extractionfollowed by extraction with ethyl acetate (10 mL)
  2. washThe organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate (10 mL)
  3. dry with materiala saturated aqueous solution of sodium chloride (10 mL), and was then dried over anhydrous magnesium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f459b887dfb74fdfb7bea82daa48dacb
Source dataset
uspto-grants-2003_12
Patent number
US06670447B2

Reaction notes

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