Hydrochloric Acid → HCID 131720045, compound

HRID 1683739Notes

Reaction equation

HRID 1683739 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][C:17]2=[CH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Cl:32]CCl>C(O)C.O>[ClH:32].[CH:22](=[C:17]1[CH2:18][CH2:19][CH2:20][CH2:21][C:16]1=[N:15][O:14][CH2:13][CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 54561569HCID 54561569, compound

Product 1

HCID 131720045HCID 131720045, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The above ester (2.5 g, 6.5 mmol) was dissolved in ethanol (20 ml) and 4N sodium hydroxide (4.9 ml) was added. The mixture was stirred at ambient temperature for 3 h and excess concentrated hydrochloric acid was added followed by dichloromethane (300 ml) and water (15 ml). The phases were separated and the organic phase was dried (MgSO4) and the solvent evaporated in vacuo. The residue was re-evaporated with acetone and recrystallised from acetone (180 ml) to give 1.5 g of the title compound as a solid.

Workup

  1. customThe phases were separated
  2. dry with materialthe organic phase was dried (MgSO4)
  3. customthe solvent evaporated in vacuo
  4. customThe residue was re-evaporated with acetone
  5. customrecrystallised from acetone (180 ml)

Sources & evidence

ORD record
ord-c281e6059b5f451d8bf96c17325aec57
Source dataset
uspto-grants-1997_06
Patent number
US05639766

Reaction notes

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