Hydrochloric Acid → HCID 57889163, compound

HRID 1394138Notes

Reaction equation

HRID 1394138 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[O:11])[CH:5]=1.O.[OH-].[Li+].Cl>C1COCC1>[CH3:16][S:13]([NH:12][C:10]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:17])=[O:2])=[O:11])(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 47269479HCID 47269479, compound

Product 1

HCID 57889163HCID 57889163, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 32A (627 mg, 2.43 mmol) and lithium hydroxide monohydrate (112 mg, 2.67 mmol) in THF (15 mL) was stirred for 12 hours at room temperature after which the pH was adjusted to 6 by addition of 1 M HCl solution (3 mL, 3 mmol). The mixture was concentrated under reduced pressure, and the residue was partitioned between dichloromethane (30 mL) and H2O (10 mL). The aqueous layer was extracted with ethyl acetate (2×20 mL), and the combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure to provide a white powder as the titled compound. MS (ESI) m/e 244 (M+H)+, 242 (M−H)−; 1H NMR (500 MHz, CD3OD) δ ppm 3.38 (s, 3H) 7.64 (t, 1H) 8.11 (m, 1H) 8.27 (m, 1H) 8.54 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between dichloromethane (30 mL) and H2O (10 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-73027ffa03f64788808d8906e038823d
Source dataset
uspto-grants-2008_03
Patent number
US07348346B2

Reaction notes

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