Sodium Hydroxide → HCID 178446242, compound

HRID 705348Notes

Reaction equation

HRID 705348 reaction equation
Cl[CH2:2][CH2:3][N:4]1C(=O)[O:7][N:6]=[C:5]1[C:10]1[C:14]2[CH:15]=[C:16]([CH:29]3[CH2:31][CH2:30]3)[C:17]([N:19]([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][C:13]=2[O:12][C:11]=1[C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1.[OH-].[Na+]>C(O)C>[CH:29]1([C:16]2[C:17]([N:19]([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][C:13]3[O:12][C:11]([C:32]4[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=4)=[C:10]([C:5]4[NH:4][CH2:3][CH2:2][O:7][N:6]=4)[C:14]=3[CH:15]=2)[CH2:30][CH2:31]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89955494HCID 89955494, compound

Product 1

HCID 178446242HCID 178446242, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of Example 10H (61 mg, 0.109 mmol) and 1.0 M sodium hydroxide (0.271 mL, 0.271 mmol) in ethanol (2 mL) was refluxed for 1 hour, cooled and partitioned between water and ethyl acetate. The organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with 1% to 4% methanol in dichloromethane to give the title compound as a solid (26 mg, 47%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.55 (m, 1H) 0.83 (m, 6H) 0.88 (m, 1H) 0.99 (m, 2H) 1.26 (m, 1H) 1.38 (m, 1H) 1.61 (m, 1H) 2.38 (m, 1H) 3.12 (s, 3H) 3.45 (m, 2H) 3.63 (m, 1H) 3.73 (m, 1H) 3.99 (t, J=4.65 Hz, 2H) 7.05 (s, 1H) 7.24 (t, J=3.20 Hz, 1H) 7.40 (m, 2H) 7.83 (s, 1H) 8.00 (m, 2H); MS (ESI+) m/z 500 (M+H)+.

Workup

  1. temperaturecooled
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel eluting with 1% to 4% methanol in dichloromethane

Sources & evidence

ORD record
ord-12cad15d06a041f08dffc130248c4fc7
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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