Hydrochloric Acid → HCID 24842616, compound

HRID 566527Notes

Reaction equation

HRID 566527 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14][CH2:15][CH2:16][N:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Cl:33]CCl>C(O)C>[ClH:33].[C:24]1([N:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12][N:8]2[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 10620784HCID 10620784, compound

Product 1

HCID 24842616HCID 24842616, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The ester prepared in Example 1 (3.5 g, 8.8 mmol) was dissolved in ethanol (10 ml) and a 12 N sodium hydroxide solution (1.5 ml) was added. The reaction mixture was stirred at room temperature for 5 h. A concentrated hydrochloric acid solution (2.2 ml) was added with cooling of the reaction vessel in an ice-bath and dichloromethane (300 ml) was added. The resulting emulsion was dried (Na2SO4) and the solvent evaporated in vacuo to give a residue which was crystallised from acetone. This afforded 1.5 g (43%) of the title compound.

Workup

  1. temperaturewith cooling of the reaction vessel in an ice-bath
  2. dry with materialThe resulting emulsion was dried (Na2SO4)
  3. customthe solvent evaporated in vacuo
  4. customto give a residue which
  5. customwas crystallised from acetone

Sources & evidence

ORD record
ord-4716831faad6477799a3f4d75ce72ffa
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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