Lithium Hydroxide → HCID 69153200, compound

HRID 1744159Notes

Reaction equation

HRID 1744159 reaction equation
[Br:1][C:2]1[C:3]([CH3:17])=[N:4][S:5][C:6]=1[NH:7][C@H:8]([C:13]([O:15]C)=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11].[OH-].[Li+]>CO>[Br:1][C:2]1[C:3]([CH3:17])=[N:4][S:5][C:6]=1[NH:7][C@H:8]([C:13]([OH:15])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69151609HCID 69151609, compound

Product 1

HCID 69153200HCID 69153200, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice cold solution of methyl N-(4-bromo-3-methylisothiazol-5-yl)-L-leucinate (11.7 g, 36.4 mmol) in methanol (300 mL) was slowly added over 10 min a 2.0 M aqueous lithium hydroxide solution (75 mL, 150 mmol). The resulting cloudy solution was stirred at room temperature for 3 hours. Most of the methanol was removed under reduced pressure and the resulting aqueous suspension was partitioned between EtOAc and water+90 ml of 10% HCl. The organic layer was washed once with water, dried over Na2SO4 and concentrated in vacuo to give N-(4-bromo-3-methylisothiazol-5-yl)-L-leucine as a white solid.

Workup

  1. customMost of the methanol was removed under reduced pressure
  2. customthe resulting aqueous suspension was partitioned between EtOAc and water+90 ml of 10% HCl
  3. washThe organic layer was washed once with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19962c07fecc4ef9b0616f125dcf38db
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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