m-Chloroperbenzoic acid → HCID 69663309, compound

HRID 1612070Notes

Reaction equation

HRID 1612070 reaction equation
[O:1]=[C:2]1[N:6]2[CH2:7][S:8][CH2:9][CH:5]2[C:4](=[O:10])[N:3]1[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]#[N:22])=[CH:13][CH:12]=1.ClC1C=C(C=CC=1)C(OO)=[O:28]>C(Cl)Cl>[O:28]=[S:8]1[CH2:9][CH:5]2[C:4](=[O:10])[N:3]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]([C:21]#[N:22])=[CH:13][CH:12]=3)[C:2](=[O:1])[N:6]2[CH2:7]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 23594037HCID 23594037, compound

Product 1

HCID 69663309HCID 69663309, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 17B (62 mg, 0.2 mmol) in CH2Cl2 (1.5 mL) was added 3chloroperoxybenzoic acid (46 mg, 0.2 mmol). The reaction was stirred at RT for 2 h, then quenched with 5% aqueous Na2S2O3 and extracted with CH2Cl2 (2×) and EtOAc (2×). The combined organic extracts were washed with saturated aqueous NaHCO3, brine, dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to give a crude product, which was chromatographed (silica gel) eluting with EtOAc/hexane (2:3) to give 6 mg of the title compound (reacemate) as a white solid. HPLC: 97% at 4.0 min (retention time) (Conditions: Zorbax SB C18 (4.6×75 mm); Eluted with 0% to 100% B, 8 min gradient. (A=90% H2O-10% MeOH-0.1% H3PO4 and B=10% H2O-90% MeOH-0.1% H3PO4); Flow rate at 2.5 mL/min. UV detection at 220 nm). MS (ES): m/z 326 [M+1]+.

Workup

  1. customquenched with 5% aqueous Na2S2O3
  2. extractionextracted with CH2Cl2 (2×) and EtOAc (2×)
  3. washThe combined organic extracts were washed with saturated aqueous NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customto give a crude product, which
  8. customwas chromatographed (silica gel)
  9. washeluting with EtOAc/hexane (2:3)

Sources & evidence

ORD record
ord-c287da0fb5d6475c8ed39850116f16ad
Source dataset
uspto-grants-2006_01
Patent number
US06992102B2

Reaction notes

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