Sodium Hydroxide → HCID 90413704, compound

HRID 1521978Notes

Reaction equation

HRID 1521978 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:28][CH3:29])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH2:22][CH2:21][CH:20]([C:23]([O:25]CC)=[O:24])[CH2:19][CH:18]=4)=[CH:16][C:9]=23)[CH:7]=1.[OH-].[Na+]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:28][CH3:29])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH2:22][CH2:21][CH:20]([C:23]([OH:25])=[O:24])[CH2:19][CH:18]=4)=[CH:16][C:9]=23)[CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 90412812HCID 90412812, compound

Product 1

HCID 90413704HCID 90413704, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of Example 219B (350 mg, 0.887 mmol) in 10 mL dioxane was added 6M aqueous sodium hydroxide (1.479 mL, 8.87 mmol). The mixture was heated at 50° C. for 12 hours, cooled and diluted with 25 mL water. The basic aqueous layer was extracted with ethyl acetate (twice) and the organics were discarded. To the basic aqueous layer was added 25 mL ethyl acetate and the aqueous layer made slightly acidic with 2.5M hydrochloric acid. The aqueous layer was extracted with ethyl acetate (twice) and the combined organics were washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 1.60-1.77 (m, 1H) 1.99-2.12 (m, 1H) 2.28-2.46 (m, 3H) 2.53 (dd, J=7.78, 2.90 Hz, 2H) 3.62-3.89 (m, 3H) 6.18 (d, J=1.83 Hz, 1H) 6.53 (s, 1H) 7.02 (d, J=4.88 Hz, 1H) 7.08-7.42 (m, 3H) 8.17 (d, J=4.88 Hz, 1H) 11.73 (d, J=1.53 Hz, 1H) 11.96-12.37 (m, J=2.44 Hz, 1H); MS (ESI): 367.2 (M+H)+.

Workup

  1. temperaturecooled
  2. extractionThe basic aqueous layer was extracted with ethyl acetate (twice) and the
  3. additionTo the basic aqueous layer was added 25 mL ethyl acetate
  4. extractionThe aqueous layer was extracted with ethyl acetate (twice) and the combined
  5. washorganics were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bdc6c214253f4dcaa492643a258012fb
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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