Hydrochloric Acid → HCID 69245724, compound

HRID 2371110Notes

Reaction equation

HRID 2371110 reaction equation
[OH-].[Li+].C([O:11][CH:12]([CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:38][CH:37]=1)[CH:13]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:14][CH2:15][NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18])(=O)C1C=CC=CC=1.Cl>O1CCCC1.CO.O.O>[C:39]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:40]=[CH:41][C:36]([CH2:35][CH2:34][CH:12]([OH:11])[CH:13]([CH2:14][CH2:15][NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69242742HCID 69242742, compound

Product 1

HCID 69245724HCID 69245724, compoundYield 112.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Aqueous solution of lithium hydroxide (18 mg in 1 ml of water) was added to a solution of the compound (100 mg) obtained from Step 3 above in tetrahydrofuran:methanol:water (3:1:1, 5 ml). The resulting reaction mixture was stirred overnight. The reaction mixture was concentrated and the residue thus obtained was diluted with water, acidified with dilute hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with distilled water and brine solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure to furnish the title compound (94 mg).

Workup

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

Sources & evidence

ORD record
ord-7d0f2668b0ea435da59669b412d78fe6
Source dataset
uspto-grants-2014_04
Patent number
US08710261B2

Reaction notes

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