Lithium Hydroxide → (2R)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-naphthalen-2-ylpropanoic acid

HRID 849876Notes

Reaction equation

HRID 849876 reaction equation
C[O:2][C:3](=[O:25])[C@H:4]([N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH3:17])[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1.[OH-].[Li+].S([O-])(O)(=O)=O.[Na+]>O1CCOCC1.O.C(OCC)(=O)C>[C:21]([O:20][C:18]([N:16]([C@H:4]([CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)[C:3]([OH:25])=[O:2])[CH3:17])=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

7

Reactant 3

HCID 3939Lithium HydroxideHCID 516919Sodium BisulfateHCID 53638899HCID 53638899, compound

Product 1

HCID 10065151(2R)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-naphthalen-2-ylpropanoic acidYield 93.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

(2R)-2-(N-tert-Butoxycarbonyl-N-methylamino)-3-(2-naphthyl)propionic acid methylester (15.0 g; 43.73 mmol) was dissolved in dioxane (150 ml) and cooled on an icebath. Water (115 ml) and lithium hydroxide (1.15 g; 48.10 mmol) were added. The reaction mixture was stirred 4 hours at room temperature. Ethyl acetate (300 ml) and water (200 ml) were added. Sodium hydrogensulfate (3%) was added until acidic reaction (pH=2.5). The organic phase was washed with water (200 ml) and dried (Magnesium sulfate). The solvent was removed in vacuo to afford 13.5 g of (2R)-2-(N-tert-Butoxycarbonyl-N-methylamino)-3-(2-naphthyl)propionic acid.

Workup

  1. temperaturecooled on an icebath
  2. washThe organic phase was washed with water (200 ml)
  3. dry with materialdried (Magnesium sulfate)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2ab24166e6a3471db4d09bff630191c6
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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