Hydrochloric Acid → HCID 69152959, compound

HRID 1744100Notes

Reaction equation

HRID 1744100 reaction equation
[Br:1][C:2]1[CH:3]=[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+].Cl>CO.O>[Br:1][C:2]1[CH:3]=[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69151472HCID 69151472, compound

Product 1

HCID 69152959HCID 69152959, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution composed of methyl N-(4-bromoisothiazol-5-yl)leucinate (98 mg, 0.32 mmol) in methanol (1.5 mL) at 0° C. was treated with a 2.0 M solution of lithium hydroxide (1.0 mL, 2.0 mmol). The mixture was stirred rapidly at rt for 6 h and then recooled to 0° C. prior to acidification to pH 5.5with 2.0 M hydrochloric acid in water. The reaction vessel contents were poured into water, extracted with ethyl acetate (3×) and the combined organics were washed with saturated sodium chloride solution and dried (Na2SO4). Concentration in vacuo gave 92 mg of N-(4-bromoisothiazol-5-yl)leucine as a yellow powder.

Workup

  1. customrecooled to 0° C.
  2. extractionextracted with ethyl acetate (3×)
  3. washthe combined organics were washed with saturated sodium chloride solution
  4. dry with materialdried (Na2SO4)
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-1130ebabdf314e3592e0451aeb1c2374
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

Loading…