Sodium Hydroxide → HCID 27281430, compound

HRID 488663Notes

Reaction equation

HRID 488663 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C@@H:13]([C:22]([O:24]C)=[O:23])[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C@@H:13]([C:22]([OH:24])=[O:23])[NH:14][C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69800794HCID 69800794, compound

Product 1

HCID 27281430HCID 27281430, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(4-amino-1-naphthyl)-N-(tert-butoxycarbonyl)-L-alaninate (2.4 g, 7.0 mmol) in methanol (10 mL) was added 8M aqueous NaOH (1.5 mL, 12 mmol) and the mixture was stirred at ambient temperature for 45 minutes. The mixture was concentrated under reduced pressure, taken up in water (5 mL) and extracted with diethyl ether (2×10 mL). The aqueous layer was then shaken with ethyl acetate (30 mL) and 1M HCl (13 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (1×20 mL). The combined ethyl acetate layers were washed with brine (1×5 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to provide the titled compound (1.9 g, 83%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionextracted with diethyl ether (2×10 mL)
  3. stirringThe aqueous layer was then shaken with ethyl acetate (30 mL) and 1M HCl (13 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (1×20 mL)
  6. washThe combined ethyl acetate layers were washed with brine (1×5 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-963ea83d6b394109b33446316236ee0c
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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