Hydrochloric Acid → HCID 87318544, compound

HRID 1011228Notes

Reaction equation

HRID 1011228 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:24][CH3:25])[C:11]=1[CH:12]([CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[C:13]([O:15]CC)=[O:14])[N:8]([CH2:26][C:27]([F:30])([F:29])[F:28])[CH:7]=[C:6]([C:31]([NH:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][C:42]([F:45])([F:44])[F:43])=[CH:37][C:36]=1[CH3:46])=[O:32])[C:5]2=[O:47].[Li+].[OH-].Cl>O1CCOCC1.O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:24][CH3:25])[C:11]=1[CH:12]([CH:18]1[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]1)[C:13]([OH:15])=[O:14])[N:8]([CH2:26][C:27]([F:30])([F:28])[F:29])[CH:7]=[C:6]([C:31]([NH:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][C:42]([F:43])([F:44])[F:45])=[CH:37][C:36]=1[CH3:46])=[O:32])[C:5]2=[O:47]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 91585901HCID 91585901, compound

Product 1

HCID 87318544HCID 87318544, compoundYield 98.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

60 mg (0.089 mmol) of the compound of Example 5 are stirred in 2.2 ml of dioxane and 444 μl of LiOH 1M (5 eq.) in water at RT overnight. The mixture is acidified with 1N HCl and diluted with ethyl acetate. It is extracted by shaking twice with water and once with a saturated NaCl solution. The organic phase is dried over magnesium sulfate and freed from the solvent on a rotary evaporator. The residue is dried under HV. 57 mg of the title compound (94% of theory) are obtained.

Workup

  1. customat RT
  2. customovernight
  3. extractionIt is extracted
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customfreed from the solvent on a rotary evaporator
  6. customThe residue is dried under HV

Sources & evidence

ORD record
ord-386e3d8456f9485b93394f3219e4452f
Source dataset
uspto-grants-2011_07
Patent number
US07977349B2

Reaction notes

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