Hydrochloric Acid → HCID 66814495, compound

HRID 1959992Notes

Reaction equation

HRID 1959992 reaction equation
[ClH:1].[CH2:2]([N:6]([C:37]([NH:39][C:40]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][C:41]=1[F:47])=[O:38])[CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:36]=[CH:35][C:17]([O:18][C:19]3[CH:24]=[CH:23][C:22]([N:25]([S:31]([CH3:34])(=[O:33])=[O:32])[CH2:26][C:27]([O:29]C)=[O:28])=[CH:21][CH:20]=3)=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)[CH2:3][CH2:4][CH3:5].[OH-].[Na+].Cl>CO>[ClH:1].[CH2:2]([N:6]([C:37]([NH:39][C:40]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][C:41]=1[F:47])=[O:38])[CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:36]=[CH:35][C:17]([O:18][C:19]3[CH:20]=[CH:21][C:22]([N:25]([CH2:26][C:27]([OH:29])=[O:28])[S:31]([CH3:34])(=[O:33])=[O:32])=[CH:23][CH:24]=3)=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66814284HCID 66814284, compound

Product 1

HCID 66814495HCID 66814495, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound prepared in Example 3(106) (80 mg) in methanol (1 ml) was added 2N aqueous solution of sodium hydroxide (0.5 ml). The reaction mixture was stirred for 2.5 hours at room temperature. To the reaction mixture on ice bath was added 1N hydrochloric acid until the pH of the solution was below 5, then it was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, concentrated. The obtained residue was purified by column chromatography on silica gel (dichloromethane:methanol=9:1). To a solution of the obtained compound in ethyl acetate was added 4N hydrogen chloride in ethyl acetate solution. The reaction mixture was concentrated to give the title compound (64 mg) having the following physical data.

Workup

  1. extractionit was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe obtained residue was purified by column chromatography on silica gel (dichloromethane:methanol=9:1)
  5. additionTo a solution of the obtained compound in ethyl acetate was added 4N hydrogen chloride in ethyl acetate solution
  6. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-49776713e59e4cd899f6639a17924ec6
Source dataset
uspto-grants-2013_04
Patent number
US08410276B2

Reaction notes

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