Dichloromethane → HCID 19879344, compound

HRID 1885617Notes

Reaction equation

HRID 1885617 reaction equation
C(C1C=CC(S[CH2:11][CH:12]([C:19](=[O:31])[N:20]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=CC=1)(=O)C.Cl[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([O:41]O)=O)[CH:34]=1.[S:43]([O-:46])([O-])=[O:44].[Na+].[Na+].Cl[CH2:50]Cl>>[C:39]([C:35]1[CH:34]=[CH:33][C:38]([S:43]([CH2:11][CH:12]([C:19](=[O:31])[N:20]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])(=[O:46])=[O:44])=[CH:37][CH:36]=1)(=[O:41])[CH3:50]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 19879342HCID 19879342, compound

Product 1

HCID 19879344HCID 19879344, compound

Conditions

Temperature
0 °C

Procedure

Into a solution of methyl 5-(4-acetylphenylthio)-4-(N,N-dipentylcarbamoyl)pentanoate (0.44 g) in dry dichloromethane (10 ml) were added portions of m-chloroperbenzoic acid (80%, 0.52 g) with stirring at 0° C. After stirring at room temperature for 2 hours, sodium sulfite was added. The reaction mixture was washed with a saturated sodium bicarbonate solution and water, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica by eluting with chloroform/ethanol (10:1) to give 0.45 g of methyl 5-(4-acetylphenylsulfonyl)-4-(N,N-dipentylcarbamoyl)pentanoate as an oil.

Workup

  1. stirringAfter stirring at room temperature for 2 hours
  2. washThe reaction mixture was washed with a saturated sodium bicarbonate solution and water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica
  6. washby eluting with chloroform/ethanol (10:1)

Sources & evidence

ORD record
ord-948e18f78d8b44428d41d1133e86a467
Source dataset
uspto-grants-1992_09
Patent number
US05145869

Reaction notes

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