Hydrochloric Acid → HCID 10089642, compound

HRID 129256Notes

Reaction equation

HRID 129256 reaction equation
[CH3:1][C:2]1[C:3]([C:16]([C:18]2[S:22][C:21]([C:23]([O:25]CC)=[O:24])=[CH:20][CH:19]=2)=[O:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[OH-].[K+].Cl>CO>[CH3:1][C:2]1[C:3]([C:16]([C:18]2[S:22][C:21]([C:23]([OH:25])=[O:24])=[CH:20][CH:19]=2)=[O:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 10022924HCID 10022924, compound

Product 1

HCID 10089642HCID 10089642, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of the ester 37 (50 mg, 0.13 mmol) in 75% aqueous methanol (3 mL) was added one pellet of potassium hydroxide (0.1 g). The reaction mixture was stirred at 70° C. for 1.5 h during which time the material dissolved. The solution was cooled to room temperature, acidified with 1N aqueous hydrochloric acid, and then extracted with 80% ethyl acetate/hexane. The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated to afford a white solid (46 mg). Recrystallization from methanol afforded the desired acid 38 as a white crystalline solid (42 mg, 1%): m.p. 214°-215° C. The structure of the product was also confirmed using IR, 1H NMR and mass spectroscopy

Workup

  1. dissolutiondissolved
  2. temperatureThe solution was cooled to room temperature
  3. extractionextracted with 80% ethyl acetate/hexane
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d61e626dfa084383bd7fff20135d1158
Source dataset
uspto-grants-1995_11
Patent number
US05466861

Reaction notes

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