Hydrochloric Acid → HCID 25256746, compound

HRID 1948667Notes

Reaction equation

HRID 1948667 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[C:9]([CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:18]3[C@@H:17]4[C@@H:21]([C:22]([O:24]CC)=[O:23])[C@@H:16]4[CH2:15][C:14]=3[CH:13]=2)=[CH:8][CH:7]=[CH:6][C:5]=1[C:27]1[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:34].O.Cl>C1COCC1.CO>[CH3:3][C:4]1[C:9]([CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:18]3[C@@H:17]4[C@@H:21]([C:22]([OH:24])=[O:23])[C@@H:16]4[CH2:15][C:14]=3[CH:13]=2)=[CH:8][CH:7]=[CH:6][C:5]=1[C:27]1[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:34]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59450533HCID 59450533, compound

Product 1

HCID 25256746HCID 25256746, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydroxide solution (0.69 ml, 10 N, 6.9 mmol) was added to a stirred solution of ester from Step E (0.98 g, 2.3 mmol) in THF (4 mL), methanol (4 mL), and water (2 mL) at rt under nitrogen. The mixture was stirred at 60° C. overnight. The solution was neutralized with conc. HCl (0.57 mL), concentrated to remove organic solvent. The residue was dissolved in ethanol/water (10 mL, 1:1) warmed to obtain a clear solution and then cooled in refrigerator to produce a precipitation. The solid was collected by filtration and dried in air to give the title compound as a white crystalline solid. 1H NMR (500 MHz, CDCl3): δ 7.44 (1H, d, J=7.5 Hz), 7.29 (2H, m), 7.20 (1H, dd, J=6.5, 8.5 Hz), 7.15 (1H, s), 7.14 (1H, d, J=7.5 Hz), 7.05 (1H, 7.5 Hz), 6.87 (1H, s), 6.85 (1H, dd, J=8.5, 2.0 Hz), 5.05 (2H, s), 3.31 (1H, dd, J=18, 6.5 Hz), 3.07 (1H, d, J=18 Hz), 3.00 (1H, d, J=6.5 Hz), 2.53 (1H, m), 1.99 (3H, s), 1.97 (6H, s), 1.25 (1H, t, J=2.5 Hz) ppm. MS: m/e 399 (M+1)+.

Workup

  1. concentrationconcentrated
  2. customto remove organic solvent
  3. dissolutionThe residue was dissolved in ethanol/water (10 mL, 1:1)
  4. temperaturewarmed
  5. customto obtain a clear solution
  6. temperaturecooled in refrigerator
  7. customto produce
  8. customa precipitation
  9. filtrationThe solid was collected by filtration
  10. customdried in air

Sources & evidence

ORD record
ord-1158b0dac18946989c2990b089225b6b
Source dataset
uspto-grants-2013_03
Patent number
US08399507B2

Reaction notes

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