Peracetic Acid → HCID 67185241, compound

HRID 885978Notes

Reaction equation

HRID 885978 reaction equation
[CH3:1][C:2]1([CH3:34])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[C:19]([C:22]5[CH:23]=[N:24][N:25]([CH2:27][C:28]6[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=6)[CH:26]=5)[CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1.C(OO)(=[O:37])C>C(Cl)Cl>[CH3:1][C:2]1([CH3:34])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[C:19]([C:22]5[CH:23]=[N:24][N:25]([CH2:27][C:28]6[CH:29]=[N+:30]([O-:37])[CH:31]=[CH:32][CH:33]=6)[CH:26]=5)[CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1

Participants

4

Reactant 2

HCID 6585Peracetic Acid2×HCID 44580723HCID 44580723, compound

Product 1

HCID 67185241HCID 67185241, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Example 323 (0.013 g, 0.028 mmol) in DCM (1.0 mL) was added peracetic acid (0.010 mL, 36-40 wt % in acetic acid, 0.055-0.061 mmol). The reaction mixture was stirred at r.t. for 150 minutes and then additional peracetic acid (0.040 mL, 36-40 wt % in acetic acid, 0.214-0.238 mmol) was added. After 46 h, the reaction mixture was concentrated in vacuo. Purification by preparative HPLC (Method 6) gave the title compound (0.003 g, 20%) as a white solid. δH (CDCl3) 8.19-8.13 (2H, m), 7.98 (1H, d, J 1.9 Hz), 7.78 (1H, s), 7.66 (1H, s), 7.32-7.27 (1H, m), 7.20-7.14 (2H, m), 6.97 (1H, d, J 8.5 Hz), 5.42 (1H, s), 5.33 (2H, s), 4.37-4.31 (2H, m), 4.23-4.17 (2H, m), 2.89 (2H, s), 1.41 (6H, s). LCMS (ES+) 489 (M+H)+, RT 2.48 minutes (Method 1).

Workup

  1. waitAfter 46 h
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customPurification by preparative HPLC (Method 6)

Sources & evidence

ORD record
ord-9d13633afafb4f59ae8d73aa4269b24d
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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