Hydrochloric Acid → N-(4-bromo-5-methylisoxazol-3-yl)leucine

HRID 1744107Notes

Reaction equation

HRID 1744107 reaction equation
[Br:1][C:2]1[C:3]([NH:8][C@H:9]([C:14]([O:16]C)=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][O:5][C:6]=1[CH3:7].[Li+].[OH-].Cl>CO>[Br:1][C:2]1[C:3]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH:11]([CH3:12])[CH3:13])=[N:4][O:5][C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69152086methyl N-(4-bromo-5-methylisoxazol-3-yl)leucinate

Product 1

HCID 69153233N-(4-bromo-5-methylisoxazol-3-yl)leucine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A methanol solution (25 mL) of methyl N-(4-bromo-5-methylisoxazol-3-yl)leucinate (602 mg, 1.97 mmol) and 2 M LiOH (10 ml, 20 mmol) was stirred for 50 minutes at room temperature. Ice water and aq. 10% HCl was added and the product was extracted with ethyl acetate (3×), dried over Na2SO4 and concentrated in vacuo to afford N-(4-bromo-5-methylisoxazol-3-yl)leucine which was used as is in the next step.

Workup

  1. extractionthe product was extracted with ethyl acetate (3×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-459cf0501caf48ceb3f1c864dfaa1155
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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