Hydrochloric Acid → HCID 68863989, compound

HRID 1725962Notes

Reaction equation

HRID 1725962 reaction equation
[CH2:1]([O:3][C:4]1[C:13]([CH2:14][CH3:15])=[CH:12][CH:11]=[C:10]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])(=[O:19])=[O:18])[C:5]=1[C:6]([O:8]C)=[O:7])[CH3:2].O.[OH-].[Li+].Cl>O1CCOCC1.O>[CH2:1]([O:3][C:4]1[C:13]([CH2:14][CH3:15])=[CH:12][CH:11]=[C:10]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])(=[O:18])=[O:19])[C:5]=1[C:6]([OH:8])=[O:7])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68863398HCID 68863398, compound

Product 1

HCID 68863989HCID 68863989, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Two reactions were run simultaneously. For each reaction, a solution of Example 385H (0.26 g, 0.68 mmol) and lithium hydroxide hydrate (0.275 g, 6.5 mmol) in dioxane (3 mL) and water (1.5 mL) was heated to 160° C. for 15 minutes. The combined reaction mixture was acidified to pH 2.0 with 1 N HCl and extracted with ethyl acetate. The extract was dried (MgSO4), filtered, and concentrated to provide the desired product, 0.475 g, 94.8% yield. 1H NMR (DMSO-d6) δ 1.10 (t, 3H) 1.22 (t, 3H), 2.54 (q, 2H), 3.80 (q, 2H), 6.80 (d, 1H), 7.20 (d, 1H), 7.30 (t, 1H), 7.40 (dd, 1H), 7.65-7.75 (m, 2H), 9.90 (s, 1H), 13.25 (br s, 1H); MS (ESI(−)) m/e 366 (M−H)−.

Workup

  1. customFor each reaction
  2. customThe combined reaction mixture
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0d34cc40504b45d8916cccc22ecee070
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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