Monoperoxyphthalic Acid Magnesium Salt → HCID 90708541, compound

HRID 857331Notes

Reaction equation

HRID 857331 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[S:16][CH3:17])[N:9]3[CH2:18][CH2:19][CH2:20][CH:21]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:8]=23)=[CH:4][CH:3]=1.C1C=C(C([O-])=[O:37])C(C(O[O-])=O)=CC=1.[Mg+2]>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[S:16]([CH3:17])=[O:37])[N:9]3[CH2:18][CH2:19][CH2:20][CH:21]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:8]=23)=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 10130449Monoperoxyphthalic Acid Magnesium SaltHCID 90937022HCID 90937022, compound

Product 1

HCID 90708541HCID 90708541, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the sulfide of Step 12 (270 mg, 0.6 mmol) in 30 ml of CH2Cl2/MeOH (10:1) mixture at 0° C. was added MMPP (312 mg, 0.6 mmol). The reaction mixture was stirred at 0° C. for 30 minutes and then quenched with saturated aqueous NaHCO3 and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 70% EtOAc in Hexanes to provide 210 mg as a white solid.

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluted with 70% EtOAc in Hexanes
  7. customto provide 210 mg as a white solid

Sources & evidence

ORD record
ord-66da3c3e1989452784ccbfc8788d72ab
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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