m-Chloroperbenzoic acid → HCID 59854957, compound

HRID 2375463Notes

Reaction equation

HRID 2375463 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([C@H:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][C@H:19]2[F:25])[CH3:17])=[O:15])[C@:11]([CH2:32][OH:33])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:10]=1.C1C=C(Cl)C=C(C(OO)=[O:42])C=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([C@H:18]2[CH2:23][CH2:22][N+:21]([CH3:24])([O-:42])[CH2:20][C@H:19]2[F:25])[CH3:17])=[O:15])[C@:11]([CH2:32][OH:33])([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11655511ALR-3456

Product 1

HCID 59854957HCID 59854957, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 20 mg (0.044 mmol) of 3-1 in 1 mL of CH2Cl2 at 0° C. was added 11 g (˜0.048 mmol) of mCPBA. The ice-bath was removed and the reaction was stirred for 30 min. The mixture was partitioned with EtOAc and saturated aqueous NaHCO3, separated, washed with H2O, brine, dried over Na2SO4 and concentrated by rotary evaporation. The residue was loaded onto a silica gel column and eluted with EtOAc—20:1:1 EtOH/NH4OH/H2O to provide 9-1 as a white foam. Data for 9-1: 1HNMR (500 MHz, CDCl3) δ 7.4-7.2 (m, 5H), 7.1-6.9 (nm, 3H), 6.25 (s, 1H), 5.0-4.9 (m, 2H), 4.7. (m, 1H), 4.5 (m, 1H), 4.3-4.2 (m, 1H), 4.0 (m, 2H), 3.7 (m, 1H), 3.4-3.3 (m, 2H), 3.3 (s, 3H), 3.2 (s, 3H), 2.5-1.9 (bs, 2H), 1.8 (m, 1H) ppm. HRMS (ES) calc'd M+H for C25H28F3N3O3: 476.2156. Found: 476.2165.

Workup

  1. customThe ice-bath was removed
  2. customThe mixture was partitioned with EtOAc and saturated aqueous NaHCO3
  3. customseparated
  4. washwashed with H2O, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated by rotary evaporation
  7. washeluted with EtOAc—20:1:1 EtOH/NH4OH/H2O

Sources & evidence

ORD record
ord-a5415a76112e4064ba993fc3fd6552b6
Source dataset
uspto-grants-2008_12
Patent number
US07465746B2

Reaction notes

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