Hydrochloric Acid → HCID 66671358, compound

HRID 2371112Notes

Reaction equation

HRID 2371112 reaction equation
[OH-].[Li+].C([O:11][CH:12]([CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:37][CH:36]=1)[CH:13]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:14][CH2:15][NH:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)(=O)C1C=CC=CC=1.Cl>O1CCCC1.CO.O.O>[C:38]1([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:39]=[CH:40][C:35]([CH2:34][CH2:33][CH:12]([OH:11])[CH:13]([CH2:14][CH2:15][NH:16][C:17](=[O:25])[C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[C:26]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[O:27])=[CH:36][CH:37]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66671331HCID 66671331, compound

Product 1

HCID 66671358HCID 66671358, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Aqueous solution of lithium hydroxide (22 mg) was added to a solution of the compound (120 mg) obtained from Step 1 above, in tetrahydrofuran:methanol:water (3:1:1, 5 ml) and the reaction mixture was stirred overnight. The reaction mixture was concentrated and the residue thus obtained was taken in distilled water, acidified with dilute hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with distilled water and brine solution and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to furnish the title compound (100 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue thus obtained
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with distilled water and brine solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e9a40c706ae8469eb8f99dea5872f288
Source dataset
uspto-grants-2014_04
Patent number
US08710261B2

Reaction notes

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