Hydrochloric Acid → HCID 68910158, compound

HRID 2198262Notes

Reaction equation

HRID 2198262 reaction equation
C([O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][O:11][CH2:10][C:9]=2[S:8][C:7]=1[NH:15][C:16]([C:18]12[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2)=[O:17])=[O:5])C.[OH-].[K+].Cl>C(O)C.O>[C:18]12([C:16]([NH:15][C:7]3[S:8][C:9]4[CH2:10][O:11][CH2:12][CH2:13][C:14]=4[C:6]=3[C:4]([OH:5])=[O:3])=[O:17])[CH2:27][CH:22]3[CH2:21][CH:20]([CH2:26][CH:24]([CH2:23]3)[CH2:25]1)[CH2:19]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 68904127HCID 68904127, compound

Product 1

HCID 68910158HCID 68910158, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of Example 166A (779 mg, 2.00 mmol) and solid potassium hydroxide (841 mg. 15.0 mmol) in ethanol (10 mL) and water (2 mL) was heated to reflux for 1 hour. After cooling to room temperature, 1N HCl was added to adjust the pH to 1. The mixture was extracted with ethyl acetate (4×20 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated by rotary evaporator to afford a crude powder. The product was recrystallized from ethyl acetate/hexanes to afford the title compound. MS (ESI+) m/z 362.1 (M+H)+.

Workup

  1. temperatureto reflux for 1 hour
  2. extractionThe mixture was extracted with ethyl acetate (4×20 mL)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporator
  6. customto afford a crude powder
  7. customThe product was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ab8b9dd40aa3473abfdc3bca71cdb949
Source dataset
uspto-grants-2012_12
Patent number
US08338623B2

Reaction notes

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