Hydrochloric Acid → HCID 20610773, compound

HRID 434135Notes

Reaction equation

HRID 434135 reaction equation
[C:1]([N:9]1[C@@H:13]([CH:14]([CH3:16])[CH3:15])[C:12](=[O:17])OC1=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1([CH3:28])[CH:24]=[CH:23][C:22]([C@@H:25]([NH2:27])[CH3:26])=[CH:21][CH:20]=1.CN1CCOCC1.Cl>C(OCC)(=O)C>[C:19]1([CH3:28])[CH:24]=[CH:23][C:22]([C@@H:25]([NH:27][C:12](=[O:17])[C@H:13]([CH:14]([CH3:15])[CH3:16])[NH:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH3:26])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 7015759(S)-1-(p-tolyl)ethanamineHCID 59119728HCID 59119728, compound

Product 1

HCID 20610773HCID 20610773, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(S)-3-Benzoyl-4-isopropyl-2,5-oxazolidinedione (N-benzoyl-L-valine-NCA) (100 mg, 0.40 mmol) was dissolved in ethyl acetate (2.0 mL), followed by the addition of a solution of (S)-1-(p-tolyl)ethylamine (55 mg, 0.40 mmol) and N-methylmorpholine (61 mg, 0.60 mmol) in ethyl acetate (2.0 mL) at 0° C. The resulting mixture was stirred 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 (134 mg, 98%) 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-3b67c8f3bb3b4178be65a759c89eb9ce
Source dataset
uspto-grants-2003_12
Patent number
US06670447B2

Reaction notes

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