Potassium Permanganate → HCID 131730327, compound

HRID 1948320Notes

Reaction equation

HRID 1948320 reaction equation
[O-:1][Mn](=O)(=O)=O.[K+].[Cl:7][C:8]1[C:12]([Cl:13])=[C:11]([CH3:14])[NH:10][C:9]=1[C:15]([NH:17][C@H:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:25]=[C:26]([C:32]([CH:35]=[O:36])=[CH:33][N:34]=2)[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:20][C@H:19]1[O:37][CH3:38])=[O:16]>O.CC(C)=O>[Cl:7][C:8]1[C:12]([Cl:13])=[C:11]([CH3:14])[NH:10][C:9]=1[C:15]([NH:17][C@H:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:25]=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:32]([C:35]([OH:1])=[O:36])=[CH:33][N:34]=2)[CH2:20][C@H:19]1[O:37][CH3:38])=[O:16]

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 131730328HCID 131730328, compound

Product 1

HCID 131730327HCID 131730327, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 133 mg (0.84 mmol) KMnO4 in 5 ml water was added to a solution of Cis(±)-ethyl 2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-formylisonicotinate (Example 154) in 20 ml acetone, and the mixture was stirred at room temperature for 4 h. After quenching with aqueous NaHSO3, the mixture was acidified to about pH=4 with 1N HCl and extracted twice with EtOAc. The EtOAc extracts were washed with brine, dried (MgSO4) and concentrated to give a solid that was triturated with MeOH to give 175 mg of product. MS (ES) MH+: 499 for C21H24Cl2N4O6; NMR: 1.25 (t, 3H), 1.5-1.8, (m, 3H), 2.1 (s, 3H), 3.1 (m, 3H), 3.3 (s, 3H), 3.5 (m, 1H), 4.2 (m, 2H), 4.4 (m, 1H), 4.9 (m, 1H), 6.9 (s, 1H), 7.1 (d, 1H), 8.6 (s, 1H), 12.1 (s, 1H), 13.3 (s, 1H).

Workup

  1. customAfter quenching with aqueous NaHSO3
  2. extractionextracted twice with EtOAc
  3. washThe EtOAc extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give a solid
  7. customthat was triturated with MeOH

Sources & evidence

ORD record
ord-37354e8358f14b52a3e2e8b1caed5c10
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

Loading…