Hydrochloric Acid → (2S)-2-({[benzyl(methyl)amino]carbonyl}amino)-3,3-dimethylbutanoic Acid

HRID 1174223Notes

Reaction equation

HRID 1174223 reaction equation
[CH2:1]([N:8]([CH3:21])[C:9]([NH:11][C@@H:12]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:13]([O:15]C)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].Cl>O1CCOCC1>[CH2:1]([N:8]([CH3:21])[C:9]([NH:11][C@@H:12]([C:17]([CH3:19])([CH3:18])[CH3:20])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67408150methyl(2S)-2-({[benzyl(methyl)amino]carbonyl}amino)-3,3-dimethylbutanoate

Product 1

HCID 61186392(2S)-2-({[benzyl(methyl)amino]carbonyl}amino)-3,3-dimethylbutanoic Acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution containing the product from Example 63B (0.046 g, 0.057 mmol) in dioxane (1.6 mL) was treated with an aqueous solution of lithium hydroxide (0.63 mL, 0.5 N), and the mixture was stirred at 25° C. for 16 hours. An aqueous HCl solution (0.60 mL, 1N) was added, the reaction mixture was partitioned between ethyl acetate and water, and the organic phase was washed with brine and dried over MgSO4, filtered and concentrated to give the crude product, which was used without further purification.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. washthe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b282b8235d7e4ba997e1c9477abb7793
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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