Lithium Hydroxide → HCID 54241244, compound

HRID 849848Notes

Reaction equation

HRID 849848 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.-butoxycarbonyl)methylamino)-3-phenylpropoxy)acetic acid ethyl ester (0.60 g, 1.71 mmol) was dissolved in dioxane (5 ml). A solution of lithium hydroxide (0.05 g, 2.20 mmol) in water (2 ml) was added. The solution was stirred at room temp. for 56 h. 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 1N 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 vacuo to give 0.38 g of crude ((2R)-2-((tert-butoxycarbonyl)methylamino)-3-phenylpropoxy)acetic acid, that 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 1N 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 vacuo

Sources & evidence

ORD record
ord-495f76d4d05244a5bc2bb7ae5e503400
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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