Ethanol → HCID 68456661, compound

HRID 2358628Notes

Reaction equation

HRID 2358628 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[NH:21][C:22]2[C:31]3[C:26](=[N:27][C:28]([CH3:32])=[CH:29][CH:30]=3)[N:25]=[CH:24][CH:23]=2)=[CH:9][CH:8]=1)C.CCO>[OH-].[Na+]>[CH3:20][C:17]1[CH:18]=[CH:19][C:14]([S:13][C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:33])=[O:3])=[CH:8][CH:9]=2)=[C:15]([NH:21][C:22]2[C:31]3[C:26](=[N:27][C:28]([CH3:32])=[CH:29][CH:30]=3)[N:25]=[CH:24][CH:23]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 24898188HCID 24898188, compound

Product 1

HCID 68456661HCID 68456661, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The product from Example 64 (0.246 g 0.535 mmol) was dissolved in 10 mL of 5% NaOH and 10 mL of EtOH and heated to 100° C. for 2 hrs and then stirred at room temperature for 110 hrs. At this time all the solvent was removed under vacuum and the brown oil was redissolved in water, to which 2 mL of HCl was added and a yellow precipitate formed. Precipitate collected by filtration and solid dried in under vacuum overnight (150 mg, 64%) 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.33 (s, 3H), 2.75 (s, 3H), 5.42 (s, 2H), 6.46 (d, J=7.35 Hz, 1H), 6.52 (s, 1H), 6.75 (d, J=8.46 Hz, 2H), 6.99 (d, J=8.46 Hz, 1H), 7.15-7.40 (m, J=8.46 Hz, 4H), 7.85 (s, 1H), 8.62 (s, 1H), 9.08 (d, J=8.09 Hz, 1H), 9.90 (s, 1H); MS (ESI) m/z 432 (M+H)+, (ESI−) m/z 430(M−H)−.

Workup

  1. customAt this time all the solvent was removed under vacuum
  2. dissolutionthe brown oil was redissolved in water, to which 2 mL of HCl
  3. additionwas added
  4. customa yellow precipitate formed
  5. filtrationPrecipitate collected by filtration and solid
  6. customdried in under vacuum overnight (150 mg, 64%) 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.33 (s, 3H), 2.75 (s, 3H), 5.42 (s, 2H), 6.46 (d, J=7.35 Hz, 1H), 6.52 (s, 1H), 6.75 (d, J=8.46 Hz, 2H), 6.99 (d, J=8.46 Hz, 1H), 7.15-7.40 (m, J=8.46 Hz, 4H), 7.85 (s, 1H), 8.62 (s, 1H), 9.08 (d, J=8.09 Hz, 1H), 9.90 (s, 1H)

Sources & evidence

ORD record
ord-9b22408a3a7045f6a36b25e81c66d7ee
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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