Hydrochloric Acid → HCID 45261987, compound

HRID 1614794Notes

Reaction equation

HRID 1614794 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:7]1)=[O:5])C.C(O)C.[OH-].[Na+].[ClH:36]>ClCCl>[ClH:36].[C:25]1([N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH2:16][CH2:15][CH2:14][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:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 10763979HCID 10763979, compound

Product 1

HCID 45261987HCID 45261987, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The ester prepared in Example 3 (3.4 g, 8.3 mmol) was dissolved into ethanol (10 ml) and a 12 N sodium hydroxide solution (1.5 ml) was added. The reaction mixture was stirred at room temperature for 6 h. A concentrated hydrochloric acid solution (2.3 ml) was added with cooling of the reaction vessel in an ice-bath and dichloromethane (300 ml) was added. The resulting emulsion was dried over sodium sulphate and the solvent evaporated in vacuo to give a residue which was crystallised from ethyl acetate. This afforded 2.8 g (81% of the title compound.

Workup

  1. temperaturewith cooling of the reaction vessel in an ice-bath
  2. dry with materialThe resulting emulsion was dried over sodium sulphate
  3. customthe solvent evaporated in vacuo
  4. customto give a residue which
  5. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-1c90586947c241e2b5899506cde885a6
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Reaction notes

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