Hydrochloric Acid → HCID 88380185, compound

HRID 1683733Notes

Reaction equation

HRID 1683733 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][N:15]=[C:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].[ClH:30]>C(O)C>[ClH:30].[C:22]1([CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][C:16]2=[N: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:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54484556HCID 54484556, compound

Product 1

HCID 88380185HCID 88380185, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (0.6 g, 1.6 mmol) was dissolved in ethanol (5 ml) and 4N sodium hydroxide (1.6 ml) was added. The mixture was stirred at ambient temperature for 20 h, placed on an ice-bath and excess concentrated hydrochloric acid was added. The mixture was concentrated in vacuo and dichloromethane (300 ml) was added. The phases were separated and the organic phase was washed with water (5 ml) and dried (MgSO4). The solvent was evaporated in vacuo to give 0.52 g of the title compound as an amorphous solid.

Workup

  1. customplaced on an ice-bath
  2. concentrationThe mixture was concentrated in vacuo and dichloromethane (300 ml)
  3. additionwas added
  4. customThe phases were separated
  5. washthe organic phase was washed with water (5 ml)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-988bf54172e2428888503da6c2071742
Source dataset
uspto-grants-1997_06
Patent number
US05639766

Reaction notes

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