Potassium Hydroxide → HCID 118092993, compound

HRID 708898Notes

Reaction equation

HRID 708898 reaction equation
[N+](C1C=CC(C([O:10][C@@H:11]2[C@H:15]([O:16][C:17]3[C:22]([F:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[CH:19][C:18]=3[CH2:27][N:28]([C:30]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])[CH3:29])[CH2:14][O:13][CH2:12]2)=O)=CC=1)([O-])=O.[OH-].[K+]>CO>[F:23][C:22]1[C:17]([O:16][C@H:15]2[C@@H:11]([OH:10])[CH2:12][O:13][CH2:14]2)=[C:18]([CH:19]=[C:20]([N+:24]([O-:26])=[O:25])[CH:21]=1)[CH2:27][N:28]([CH3:29])[C:30](=[O:31])[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 118101240HCID 118101240, compound

Product 1

HCID 118092993HCID 118092993, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 27D (250 mg, 0.439 mmol) in MeOH (5 mL) was added KOH (0.878 mL, 0.878 mmol) and the reaction was stirred at rt for 2 h. The reaction was concentrated and acidified with 1N HCl after addition of H2O. The sample was extracted with EtOAc (2×) and the extracts was washed with sat. NaHCO3 and brine. The solvent was removed and the residue was purified by flash column chromatography (0-60% EtOAc/hexanes) to afford 27E (172 mg, 0.409 mmol, 93% yield). MS (ESI) m/z: 421.4 (M+H)+. 1H NMR (400 MHz, CDCl3)) δ ppm 7.83-8.07 (m, 2H) 7.33 (s, 5H) 5.14 (s, 2H) 4.92-5.03 (m, 1H) 4.78 (d, J=7.91 Hz, 1H) 4.70 (d, J=14.94 Hz, 1H) 4.49-4.60 (m, 1H) 4.39 (d, J=6.15 Hz, 1H) 4.06-4.19 (m, 1H) 3.90-4.03 (m, 2H) 3.65-3.78 (m, 1H) 2.84 (s, 3H).

Workup

  1. concentrationThe reaction was concentrated
  2. additionafter addition of H2O
  3. extractionThe sample was extracted with EtOAc (2×)
  4. washthe extracts was washed with sat. NaHCO3 and brine
  5. customThe solvent was removed
  6. customthe residue was purified by flash column chromatography (0-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-806ed7cb6fa34a49a318a6d71f4e9a67
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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