Hydrochloric Acid → HCID 68865836, compound

HRID 1725982Notes

Reaction equation

HRID 1725982 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][C:6]=1[NH:15][S:16]([C:19]1[CH:23]=[CH:22][S:21][C:20]=1[C:24]([O:26]C)=[O:25])(=[O:18])=[O:17])=[O:4].O.O.[OH-].[Li+].Cl>CO>[CH3:1][O:2][C:3]([C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][C:6]=1[NH:15][S:16]([C:19]1[CH:23]=[CH:22][S:21][C:20]=1[C:24]([OH:26])=[O:25])(=[O:18])=[O:17])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 68864035HCID 68864035, compound

Product 1

HCID 68865836HCID 68865836, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of Example 463A (1.37 g, 3.36 mmol) in methanol (31 mL) and distilled water (3.5 mL) was treated with lithium hydroxide monohydrate (0.704 g, 16.78 mmol), heated to 60° C. for 30 minutes, cooled to room temperature, treated with 1N HCl, and concentrated. The aqueous layer was extracted with dichloromethane twice and the combined organic fractions were dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/e 396 (M+H)+; (ESI(−)) m/e 394 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 8.98 (br s, 1H), 7.89 (d, 1H), 7.33 (d, 1H), 7.12 (s, 2H), 3.77 (s, 3H), 2.67 (br s, 2H), 2.53 (br s, 2H), 1.65 (quint, 4H).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. extractionThe aqueous layer was extracted with dichloromethane twice
  4. dry with materialthe combined organic fractions were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-10b5df9deeb149fca45b0868351c6277
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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