m-Chloroperbenzoic acid → HCID 59644553, compound

HRID 2252011Notes

Reaction equation

HRID 2252011 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[F:12][C:13]([F:51])([F:50])[C:14]1[CH:15]=[C:16]([CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:45]=1)[CH2:17][N:18]1[C:22]([N:23]2[CH2:28][CH2:27][S:26][CH2:25][CH2:24]2)=[C:21]([C:29]2[N:33]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[Cl:41])[C:32]([CH3:42])=[N:31][N:30]=2)[N:20]=[N:19]1>C1COCC1>[F:51][C:13]([F:50])([F:12])[C:14]1[CH:15]=[C:16]([CH:43]=[C:44]([C:46]([F:47])([F:48])[F:49])[CH:45]=1)[CH2:17][N:18]1[C:22]([N:23]2[CH2:28][CH2:27][S:26](=[O:9])[CH2:25][CH2:24]2)=[C:21]([C:29]2[N:33]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[Cl:41])[C:32]([CH3:42])=[N:31][N:30]=2)[N:20]=[N:19]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86760599HCID 86760599, compound

Product 1

HCID 59644553HCID 59644553, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add m-chloro-perbenzoic acid (29 mg, 0.13 mmol) to a solution of 4-{3-(3,5-bis-trifluoromethyl-benzyl)-5-[4-(2-chloro-benzyl)-5-methyl-4H-[1,2,4]triazol-3-yl]-3H-[1,2,3]triazol-4-yl}-thiomorpholine (69 mg, 0.11 mmol) in THF (1 mL) at −78° C. After 30 minutes, quench with 1N Na2S2O3 at −78° C., warm to RT. Dilute with 20% i-PrOH/CHCl3, wash with 1N HCl, saturated NaHCO3 solution, and brine. Dry the combined organic layers over MgSO4 and concentrate. Purify the residue by flash chromatography on silica gel eluting with 0-4% MeOH/CHCl3 to afford the title compound: MS(IS) 618 (M+1). TLC: Rf=0.18 (5% MeOH/CHCl3).

Workup

  1. customquench with 1N Na2S2O3 at −78° C.
  2. additionDilute with 20% i-PrOH/CHCl3
  3. washwash with 1N HCl, saturated NaHCO3 solution, and brine
  4. dry with materialDry the combined organic layers over MgSO4
  5. concentrationconcentrate
  6. customPurify the residue by flash chromatography on silica gel eluting with 0-4% MeOH/CHCl3

Sources & evidence

ORD record
ord-22068b5109de4fdf94b937432921a04b
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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