Bromine → 3-Methyl-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)pentanoic acid

HRID 3691Notes

Reaction equation

HRID 3691 reaction equation
C(C(NC([C:12]1[CH:36]=[CH:35][CH:34]=[CH:33][C:13]=1[C:14]([N:16]([S:25]SC1C=CC=CC=1)[CH:17]([CH:21]([CH3:24])[CH2:22][CH3:23])[C:18]([OH:20])=[O:19])=[O:15])=O)C(C)CC)(O)=O.BrBr>ClCCl>[CH3:24][CH:21]([CH2:22][CH3:23])[CH:17]([N:16]1[C:14](=[O:15])[C:13]2[CH:33]=[CH:34][CH:35]=[CH:36][C:12]=2[S:25]1)[C:18]([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 24408BromineHCID 867540052-[2-(1-Carboxy-2-methylbutylcarbamoyl) phenyldisulfanylbenzoylamino]-3-methylpentanoic acid

Product 1

HCID 178926623-Methyl-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)pentanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred, room temperature suspension of 5.3 g (10.0 mmol) of [S-(R*,R*)]-2-[2-[2-(1-carboxy-2-methylbutylcarbamoyl)phenyldisulfanyl benzoylamino]-3-methylpentanoic acid (prepared by the general method of Example 5) in 200 mL of dichloromethane was treated dropwise with 2.4 g (15.0 mmol) of liquid bromine. The reaction mixture was stirred at room temperature for 2 hours, and the solvent was evaporated in vacuo. The residue was triturated with dichloromethane, which was also evaporated in vacuo to remove excess bromine. The residue was partitioned between dichloromethane/5% sodium bicarbonate (200 mL each). The aqueous layer was separated, washed with dichloromethane, and acidified to pH 1.5 with 6.0M hydrochloric acid. After extracting with dichloromethane (2×75 mL), the combined organic layers were washed with water, dried (MgSO4), filtered and evaporated in vacuo to give 4.8 g of the title compound, mp 50°-52° C.

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was triturated with dichloromethane, which
  3. customwas also evaporated in vacuo
  4. customto remove excess bromine
  5. customThe residue was partitioned between dichloromethane/5% sodium bicarbonate (200 mL each)
  6. customThe aqueous layer was separated
  7. washwashed with dichloromethane
  8. extractionAfter extracting with dichloromethane (2×75 mL)
  9. washthe combined organic layers were washed with water
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-715eda2fd48842e6980bb6bc0bfdb8f4
Source dataset
uspto-grants-1998_03
Patent number
US05734081

Reaction notes

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