Methanol → HCID 68310868, compound

HRID 1504956Notes

Reaction equation

HRID 1504956 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][C:20]2[NH:21][CH2:22][CH2:23][N:24]=2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=O.[K+].CO>C(#N)C>[CH2:1]([O:8][C:9](=[O:25])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][C:20]2[NH:21][CH:22]=[CH:23][N:24]=2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 516875Potassium PermanganateHCID 86711811HCID 86711811, compound

Product 1

HCID 68310868HCID 68310868, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 56 (274 mg, 0.81 mmol) was first dissolved in acetonitrile (10 mL), with potassium permanganate (192 mg, 1.22 mol) and alumina (567 mg, 0.3 mol) added into the solution in batch. After stirring the resulting mixture at room temperature for 40 min, CH3OH (1 mL) was added to reduce excess oxidant. The mixture was filtered and the solid material was washed with DCM:CH3OH=10:1. The filtrate was evaporated and the resulting crude material was purified with silica gel column chromatography (PE:EtOAc:TEA=3:1:0.2) to give compound 57 (110 mg, 41%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ7.32-7.43 (m, 6H), 7.28 (d, 2H, J=8.3 Hz), 7.09 (d, 2H, J=8.3 Hz), 6.90-9.95 (m, 2H), 6.70 (br s, 1H), 5.19 (s, 2H), 2.65 (t, 2H, J=7.4 Hz), 2.62 (d, 2H, J=7.4 Hz), 1.98-2.07 (m, 2H).

Workup

  1. additionadded into the solution in batch
  2. filtrationThe mixture was filtered
  3. washthe solid material was washed with DCM
  4. customThe filtrate was evaporated
  5. customthe resulting crude material was purified with silica gel column chromatography (PE:EtOAc:TEA=3:1:0.2)

Sources & evidence

ORD record
ord-dddd7fbe71974f0b98983d777db93c71
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

Loading…