Water → HCID 22448951, compound

HRID 2186753Notes

Reaction equation

HRID 2186753 reaction equation
[C:1]1([C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([S:9][CH2:10][CH2:11][N:12]2[C:17]3[CH:18]=[CH:19][CH:20]=[C:21]([O:22][CH2:23][C:24]([OH:26])=[O:25])[C:16]=3[O:15][CH2:14][CH2:13]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:41])C=1.O>C(Cl)Cl>[C:27]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([S:9]([CH2:10][CH2:11][N:12]2[C:17]3[CH:18]=[CH:19][CH:20]=[C:21]([O:22][CH2:23][C:24]([OH:26])=[O:25])[C:16]=3[O:15][CH2:14][CH2:13]2)=[O:41])[CH3:8])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 9803776HCID 9803776, compound

Product 1

HCID 22448951HCID 22448951, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-(2-(1,1-diphenylethylthio)ethyl)-3,4-dihydro-2H-1,4-benzoxazin-8-yloxy)acetic acid (51 mg) was dissolved in methylene chloride (5 ml), and the resultant solution was stirred at room temperature. m-CPBA (20 mg) was then added to the solution, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was added to water (20 ml), and then extracted with ethyl acetate. The resultant organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was purified by Lober® column chromatography (DIOL, type A, developing solvent: n-hexane/ethyl acetate=1/2) to obtain the object compound (43 mg, yield 81%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe resultant organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by Lober® column chromatography (DIOL, type A, developing solvent: n-hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-5f1b088fa086423fb16dbe3b83d93691
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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