Methyl bromoacetate → HCID 20765987, compound

HRID 984128Notes

Reaction equation

HRID 984128 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7](=[O:10])[NH:8][O:9][C:5]=2[CH:4]=1.Br[CH2:14][C:15]([O:17][CH3:18])=[O:16]>C1COCC1>[CH3:18][O:17][C:15](=[O:16])[CH2:14][N:8]1[C:7](=[O:10])[C:6]2[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[O:9]1

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 114125776-Methoxy-1,2-benzisoxazol-3(2H)-one

Product 1

HCID 20765987HCID 20765987, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The KN(TMS)2 (7.2 g) was added to a solution of compound 22B (4 g) in 150 mL of THF at 0° C. by portion, another one hour at 0° C. with stirring. Methyl bromoacetate (7 g) was added, stirred at RT overnight. The reaction mixture was quenched with 150 mL of ethyl acetate and 100 mL of 2N HCl. The organic layer was separated, washed with water, brine, dried (MgSO4), concentrated to afford an off-white solid compound 22C (2.5 g). mp 185-188° C.; MS: 238 (M+1)+. Preparation of 5-Chlorosulfonyl-6-methoxy-3-oxo-3H-benzo[d]isoxazol-2-yl-acetic acid methyl ester (Compound 22D)

Workup

  1. stirringstirred at RT overnight
  2. customThe reaction mixture was quenched with 150 mL of ethyl acetate and 100 mL of 2N HCl
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f3afd7220bd44eada58242f247fe0ed3
Source dataset
uspto-grants-2005_03
Patent number
US06867224B2

Reaction notes

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