Hydrochloric Acid → HCID 11856285, compound

HRID 2371113Notes

Reaction equation

HRID 2371113 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(C)(C)C)=[O:28])[CH2:14][CH2:15][NH:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)=[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:38]=[CH:37][C:36]([CH2:35][CH2:34][CH:12]([OH:11])[CH:13]([CH2:14][CH2:15][NH:16][C:17]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)=[O:18])[C:27]([OH:29])=[O:28])=[CH:41][CH:40]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66671234HCID 66671234, compound

Product 1

HCID 11856285HCID 11856285, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Aqueous solution of lithium hydroxide (22 mg in 1 ml) was added to the solution of the compound (130 mg) obtained from Step 1 above, in tetrahydrofuran:methanol:water (3:1:1, 5 ml) and the reaction mixture was stirred at 40° C. 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 (40 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-f4fa5b7d4b4143e59f34b2c61e4f079a
Source dataset
uspto-grants-2014_04
Patent number
US08710261B2

Reaction notes

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