Hydrochloric Acid → HCID 178441263, compound

HRID 253640

Reaction equation

HRID 253640 reaction equation
[CH2:1]([C:5]1=[CH:6][N:7]([C:25]([CH3:28])([CH3:27])[CH3:26])[S:8]/[C:9]/1=[N:10]\[C:11]([C:13]1([CH3:24])[CH2:17][CH2:16][CH:15]([C:18]([O:20]C)=[O:19])[C:14]1([CH3:23])[CH3:22])=[O:12])[CH2:2][CH2:3][CH3:4].[OH-].[K+].C(O)C.Cl>O>[CH2:1]([C:5]1=[CH:6][N:7]([C:25]([CH3:26])([CH3:28])[CH3:27])[S:8]/[C:9]/1=[N:10]\[C:11]([C:13]1([CH3:24])[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[C:14]1([CH3:23])[CH3:22])=[O:12])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 178441264HCID 178441264, compound

Product 1

HCID 178441263HCID 178441263, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a 20-mL scintillation vial containing a magnetic stir bar were added the product from Example 92C (102 mg, 0.250 mmol) and potassium hydroxide (84 mg, 1.50 mmol). Ethanol (1 mL) and water (0.25 mL) were added. The vial was heated to 60° C. and the reaction mixed for 24 hours. After cooling to room temperature, the pH was adjusted to 1 by addition of 1N hydrochloric acid. The mixture was extracted with dichloromethane (3×10 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated by rotary evaporator to afford a tan solid. The product was recrystallized from ethyl acetate/hexanes to afford 74 mg (75%) of the title compound. 1H NMR (DMSO-d6) δ 0.63 (br s, 3H), 0.91 (t, J=7.3 Hz, 3H), 1.23-1.38 (m, 8H), 1.57-1.68 (m, 12H), 1.76-1.87 (m, 1H), 2.00-2.11 (m, 1H), 2.65-2.84 (m, 4H), 8.7 (br s, 1H), 11.7 (br s, 1H). MS (ESI+) m/z 395 (M+H)+.

Workup

  1. additionTo a 20-mL scintillation vial containing a magnetic stir bar
  2. additionthe reaction mixed for 24 hours
  3. temperatureAfter cooling to room temperature
  4. extractionThe mixture was extracted with dichloromethane (3×10 mL)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporator
  8. customto afford a tan solid
  9. customThe product was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-70fa796f956e4185b2aee697cbb969d4
Source dataset
uspto-grants-2011_01
Patent number
US07872033B2

Linked notes

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