Hydrochloric Acid → HCID 67713580, compound

HRID 1451504Notes

Reaction equation

HRID 1451504 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]/[C:16](/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:17]\[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].[ClH:32]>C(O)C.ClCCl>[ClH:32].[C:24]1(/[C:16](=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)/[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 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67713861HCID 67713861, compound

Product 1

HCID 67713580HCID 67713580, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

The above ester (3.15 g, 8 mmol) was dissolved in absolute ethanol (25 ml) and 4N sodium hydroxide (4.0 ml) was added. After stirring at ambient temperature for 4.5 h the mixture was diluted with dichloromethane (400 ml), cooled to 0° C. and 4N hydrochloric acid (7.5 ml) was added. The mixture was dried (Na2SO4) and the solvent evaporated in vacuo. The residue was re-evaporated with acetone, suspended in diethylether and stirred for 21 days to give an amorphous solid which was triturated 16 h with anhydrous diethylether. This afforded 2.1 g of the title compound as an amorphous solid.

Workup

  1. temperaturecooled to 0° C.
  2. dry with materialThe mixture was dried (Na2SO4)
  3. customthe solvent evaporated in vacuo
  4. customThe residue was re-evaporated with acetone
  5. stirringstirred for 21 days
  6. customto give an amorphous solid which
  7. customwas triturated 16 h with anhydrous diethylether

Sources & evidence

ORD record
ord-de712e57feb642d28bca4ef9bac60126
Source dataset
uspto-grants-1997_02
Patent number
US05604242

Reaction notes

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