Hydrochloric Acid → HCID 57780986, compound

HRID 1011227Notes

Reaction equation

HRID 1011227 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:23][CH3:24])[C:11]=1[N:12]1[CH2:17][CH2:16][CH:15]([C:18]([O:20]CC)=[O:19])[CH2:14][CH2:13]1)[N:8]([CH2:25][CH2:26][F:27])[CH:7]=[C:6]([C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][C:39]([F:42])([F:41])[F:40])=[CH:34][C:33]=1[CH3:43])=[O:29])[C:5]2=[O:44].[OH-].[Li+].Cl>O1CCOCC1.C(OCC)(=O)C.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:23][CH3:24])[C:11]=1[N:12]1[CH2:13][CH2:14][CH:15]([C:18]([OH:20])=[O:19])[CH2:16][CH2:17]1)[N:8]([CH2:25][CH2:26][F:27])[CH:7]=[C:6]([C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][C:39]([F:42])([F:40])[F:41])=[CH:34][C:33]=1[CH3:43])=[O:29])[C:5]2=[O:44]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57781005HCID 57781005, compound

Product 1

HCID 57780986HCID 57780986, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

60 mg (0.096 mmol) of the compound of Example 4 are dissolved in 2.35 ml of dioxane, 480 μl (5 eq.) of a 1M solution of lithium hydroxide are added, and the mixture is stirred at RT until the reaction is complete (4 h). The reaction mixture is acidified with 1N hydrochloric acid and diluted with ethyl acetate and water. Following phase separation, the organic phase is washed once again with water and then with a saturated sodium chloride solution, dried over magnesium sulfate and freed from solvents on a rotary evaporator. The residue is dried under high vacuum. 54 mg (94% of theory) of the title compound are obtained.

Workup

  1. custom(4 h)
  2. customFollowing phase separation
  3. washthe organic phase is washed once again with water
  4. dry with materialwith a saturated sodium chloride solution, dried over magnesium sulfate
  5. customfreed from solvents on a rotary evaporator
  6. customThe residue is dried under high vacuum

Sources & evidence

ORD record
ord-915291128ce9417094a5cafe476c59c8
Source dataset
uspto-grants-2011_07
Patent number
US07977349B2

Reaction notes

Loading…