Hydrochloric Acid → HCID 25195830, compound

HRID 1876346Notes

Reaction equation

HRID 1876346 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][CH2:6][C@@H:7]1[CH2:11][S:10][C:9]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[NH:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[N:8]1)C.[OH-].[Na+].Cl>O1CCCC1.CO>[CH:23]1([NH:22][C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[C:19]3[C:14]=2[NH:13][C:12]([C:9]2[S:10][CH2:11][C@@H:7]([CH2:6][CH2:5][C:4]([OH:28])=[O:3])[N:8]=2)=[CH:20]3)[CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25195829HCID 25195829, compound

Product 1

HCID 25195830HCID 25195830, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound (300 mg, 0.75 mmol) prepared in Example 157 was dissolved in tetrahydrofuran (25 ml) and methanol (25 ml). 1N aqueous sodium hydroxide solution (4.0 ml, 4 mmol) was added thereto, and the mixture was stirred for 3 h at room temperature. After completion of the reaction, 1N hydrochloric acid was added. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure, and purified by column chromatography to give the title compound (235 mg, Yield 84%).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationThe filtrate was distilled under reduced pressure
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-b9caf4919a2b4ae29ca2d3c3be6dfd88
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

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