Hydrochloric Acid → HCID 68866386, compound

HRID 1725952Notes

Reaction equation

HRID 1725952 reaction equation
[Br:1][C:2]1[C:3]([O:29][CH3:30])=[C:4]([C:15]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[F:28])(=[O:21])=[O:20])=[CH:16][CH:17]=1)[C:5]([O:7]CC1C=CC=CC=1)=[O:6].[OH-].[Li+].O1CCOCC1.Cl>O>[Br:1][C:2]1[C:3]([O:29][CH3:30])=[C:4]([C:15]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[F:28])(=[O:21])=[O:20])=[CH:16][CH:17]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 68864115HCID 68864115, compound

Product 1

HCID 68866386HCID 68866386, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Example 318C (150 mg, 0.3 mmol), lithium hydroxide (127 mg, 3.0 mmol), dioxane (3 mL), and water (1.5 mL) was sealed in a vial and microwaved at 160° C. for 15 minutes. The mixture was acidified to pH 1 with 1M HCl and extracted with ethyl acetate. The ethyl acetate was washed with brine, dried (Na2SO4), filtered, and concentrated to an oil which was triturated with 1:1 hexanes/diethyl ether to provide the desired product. MS (ESI(+)) m/e 404, 406 (M+H)+, 421, 423 (M+NH4)+, 426, 428 (M+Na)+; (ESI(−)) m/e 402, 404 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 13.48 (br s, 1H), 10.34 (br s, 1H), 7.72 (m, 2H), 7.63 (d, 1H), 7.41 (m, 1H), 7.34 (m, 1H), 6.89 (d, 1H), 3.75 (s, 3H).

Workup

  1. custommicrowaved at 160° C. for 15 minutes
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to an oil which
  7. customwas triturated with 1:1 hexanes/diethyl ether

Sources & evidence

ORD record
ord-61ca522d4a8145158bbfec18b4c56747
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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