Lithium Hydroxide → HCID 54241244, compound

HRID 1268598Notes

Reaction equation

HRID 1268598 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][O:6][CH2:7][C@H:8]([NH:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)C.[OH-].[Li+].C(OCC)(=O)C>O1CCOCC1.O>[C:21]([O:20][C:18]([CH2:17][NH:16][C@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:7][O:6][CH2:5][C:4]([OH:25])=[O:3])=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 54367719HCID 54367719, compound

Product 1

HCID 54241244HCID 54241244, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

((2R)-2-(tert-butoxycarbonylmethylamino)-3-phenylpropoxyl)-acetic acid ethyl ester (0.60 g, 1.71 mmol) was dissolved in dioxane (5 mL). A solution of lithium hydroxide (0.05g, 2.20 mmol) in water (2 mL) was added. The solution was stirred at room temperature for 56 hours. Ethyl acetate (10 mL) and water (2 mL) were added. The phases were separated. The aqueous phase was extracted with ethyl acetate (10 mL). The combined organic layers were extracted with 1 N sodium hydroxide solution (20 mL). The combined aqueous phases were acidified with a 1M sodium hydrogensulfate solution (pH 2) and extracted with ethyl acetate (2×20 mL). These ethyl acetate layers were combined and dried over magnesium sulfate. The solvent was removed in vacuum to give 0.38 g of crude ((2R)-2-(tert-butoxycarbonylmethylamino)-3-phenylpropoxy)acetic acid, which was used for the following steps.

Workup

  1. customThe phases were separated
  2. extractionThe aqueous phase was extracted with ethyl acetate (10 mL)
  3. extractionThe combined organic layers were extracted with 1 N sodium hydroxide solution (20 mL)
  4. extractionextracted with ethyl acetate (2×20 mL)
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed in vacuum

Sources & evidence

ORD record
ord-7b0353dea4ae4ad49bc54de289dd5801
Source dataset
uspto-grants-2003_04
Patent number
US06555570B2

Reaction notes

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