Hydrochloric Acid → HCID 24842608, compound

HRID 2226743Notes

Reaction equation

HRID 2226743 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][CH:16]=[C:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][CH2:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)[CH2:7]1)=[O:5])C.[OH-].[Na+].[Cl:34]CCl.Cl>C(O)C>[ClH:34].[CH:28]1[C:19]2[CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:17](=[CH:16][CH2:15][O:14][CH2:13][CH2:12][N:8]3[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]3)[C:18]=2[CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 11811846HCID 11811846, compound

Product 1

HCID 24842608HCID 24842608, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (1.7 g, 4.1 mmol) was dissolved in ethanol (15 ml) and a 4 N sodium hydroxide solution (3.5 ml) was added. The mixture was stirred vigorously at room temperature for 5 h. Dichloromethane (300 ml) was added followed by a 4 N hydrochloric acid solution until pH 1. The mixture was stirred vigorously for a few minutes and the phases were separated. The organic phase was dried over sodium sulphate and the solvent was evaporated in vacuo. The residue was re-evaporated twice with acetone, once with ethyl acetate and once with diethyl ether to give 1.7 g of the title compound as a solid which was recrystallized from acetone.

Workup

  1. stirringThe mixture was stirred vigorously for a few minutes
  2. customthe phases were separated
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was re-evaporated twice with acetone, once with ethyl acetate and once with diethyl ether

Sources & evidence

ORD record
ord-da81ea3d27324499b5425accd6d71869
Source dataset
uspto-grants-1994_09
Patent number
US05348965

Reaction notes

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