Hydrochloric Acid → HCID 67723202, compound

HRID 1682552Notes

Reaction equation

HRID 1682552 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][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].[ClH:29].O>C(O)C>[ClH:29].[C:21]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[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:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 54333729HCID 54333729, compound

Product 1

HCID 67723202HCID 67723202, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (2.0 g, 5.7 mmol) was dissolved in ethanol (25 ml) and 4N sodium hydroxide (6.4 ml) was added. The mixture was stirred at ambient temperature for 3 h. Excess concentrated hydrochloric acid was added followed by a small portion of water. The mixture was concentrated in vacuo and dichloromethane (100 ml) and water (25 ml) were added. The phases were separated and the organic phase was dried (Na2S4). The solvent was evaporated in vacuo to give a solid residue which was recrystallised from acetone to give 1.2 g of title compound as a solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo and dichloromethane (100 ml) and water (25 ml)
  2. additionwere added
  3. customThe phases were separated
  4. customthe organic phase was dried (Na2S4)
  5. customThe solvent was evaporated in vacuo
  6. customto give a solid residue which
  7. customwas recrystallised from acetone

Sources & evidence

ORD record
ord-54f934193e0e48b3a52bb999255e78f6
Source dataset
uspto-grants-1997_06
Patent number
US05635518

Reaction notes

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