Sodium Hydroxide → HCID 178490931, compound

HRID 705345Notes

Reaction equation

HRID 705345 reaction equation
ClC[CH2:3][N:4]1[C:8](=O)[O:7][N:6]=[C:5]1[C:10]1[C:14]2[CH:15]=[C:16]([CH:33]3[CH2:35][CH2:34]3)[C:17]([N:19]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][C:13]=2[O:12][C:11]=1[C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=1.[OH-].[Na+]>C(O)C>[CH:33]1([C:16]2[C:17]([N:19]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][C:13]3[O:12][C:11]([C:36]4[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=4)=[C:10]([C:5]4[NH:4][CH2:3][CH2:8][O:7][N:6]=4)[C:14]=3[CH:15]=2)[CH2:34][CH2:35]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89955642HCID 89955642, compound

Product 1

HCID 178490931HCID 178490931, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of Example 8E (3.54 g, 5.78 mmol) and 1.0 M aqueous sodium hydroxide (14.46 mL, 14.46 mmol) in ethanol (50 mL) was refluxed for 2 hours, 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 on silica gel eluting with methanol (2% to 4%) in dichloromethane to give the title compound as a solid (2.13 g, 67%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.16-0.27 (m, 1H) 0.65-0.82 (m, 2H) 0.85-1.00 (m, 1H) 2.15-2.25 (m, 1H) 3.20 (s, 3H) 3.66-3.69 (m, 3H) 4.54 (s, 2H) 4.69-4.91 (m, 2H) 6.77-6.82 (m, 2H) 7.03 (s, 1H) 7.10-7.16 (m, 2H) 7.37-7.45 (m, 2H) 7.80 (s, 1H) 7.83-7.91 (m, 2H) 11.32 (s, 1H); MS (ESI+) m/z 550.1 (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 on silica gel eluting with methanol (2% to 4%) in dichloromethane

Sources & evidence

ORD record
ord-1216a8bdd2444540a5363a3269b1e25a
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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