m-Chloroperbenzoic acid → Tert-butyl 4-{[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethylcarbamate

HRID 990078Notes

Reaction equation

HRID 990078 reaction equation
[CH2:1]([C:8]1[O:12][N:11]=[C:10]([CH2:13][S:14][C:15]2[CH:30]=[CH:29][C:18]([CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:17][CH:16]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:39])C=1>ClCCl>[CH2:1]([C:8]1[O:12][N:11]=[C:10]([CH2:13][S:14]([C:15]2[CH:16]=[CH:17][C:18]([CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[CH:29][CH:30]=2)=[O:39])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12044206Tert-butyl 4-{[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfanyl}phenethylcarbamate

Product 1

HCID 12044207Tert-butyl 4-{[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethylcarbamateYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the sulfide of Example 20 (1.00 g, 2.35 mmol) in dichloromethane (12 mL) at 0° C. was added purified mCPBA (0.423 g, 2.45 mmol) in dichloromethane (5 mL). After 1 h the ice/water bath was remove and the reaction was run for 1 h more. TLC shows no starting material and one slower running product spot. Additional dichloromethane was added and the mixture was washed with dilute aqueous sodium dithionite (1×) followed by 50% aqueous sodium bicarbonate (2×). The organic phase was dried (Na2SO4), filtered and evaporated. The residue was taken up into a solution of dichloromethane and diethyl ether and passed through a 5 cm pad of silica gel. Thorough removal of solvent in vacuo afforded 0.928 g of the title compound as a white solid.

Workup

  1. customAfter 1 h the ice/water bath was remove
  2. additionAdditional dichloromethane was added
  3. washthe mixture was washed with dilute aqueous sodium dithionite (1×)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThorough removal of solvent in vacuo

Sources & evidence

ORD record
ord-b7bdb75ba1bb4154bf1d9d7629ab6a59
Source dataset
uspto-grants-2002_10
Patent number
US06458817B1

Reaction notes

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