Hydrochloric Acid → HCID 68457989, compound

HRID 2358517Notes

Reaction equation

HRID 2358517 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][C:25]3([CH2:31]C#N)[CH2:29][O:28]C(=O)[NH:26]3)=[C:18]([Cl:34])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:35].[Na+].Cl.[CH2:38]([OH:40])C>>[ClH:34].[NH2:26][C:25]([CH2:29][OH:28])([CH2:24][CH2:23][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([S:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:10]=2)=[CH:17][C:18]=1[Cl:34])[CH2:31][C:38]([OH:40])=[O:35]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 57535900HCID 57535900, compound

Product 1

HCID 68457989HCID 68457989, compound

Procedure

To the compound of Example 146 (196 mg), a 3 mol/L aqueous solution of sodium hydroxide (5 mL) and ethanol (0.5 mL) were added and the mixture was refluxed for 8 hours. While the mixture was stirred in an ice bath, 4 mol/L hydrochloric acid was added to adjust the pH of the mixture to 2 to 1. Using ethyl acetate and water, the mixture was separated into an organic phase and an aqueous phase. The organic layer was dried over anhydrous sodium sulfate, was concentrated, and was dried in a vacuum pump to give the desired product as a pale white solid (201 mg).

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. customUsing ethyl acetate and water, the mixture was separated into an organic phase
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationwas concentrated
  5. customwas dried in a vacuum pump

Sources & evidence

ORD record
ord-a36dda97adb14f409af1977e34ed21c1
Source dataset
uspto-grants-2010_07
Patent number
US07763752B2

Reaction notes

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