Sodium Hydroxide → HCID 13543945, compound

HRID 904673Notes

Reaction equation

HRID 904673 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:13]2[C:8](=[C:9]([CH2:24][CH2:25][CH3:26])[C:10]3[O:17][C:16]([C:18]([O:20]CC)=[O:19])=[CH:15][C:14](=[O:23])[C:11]=3[CH:12]=2)[N:7]=[C:6]([C:27]([O:29]CC)=[O:28])[C:5]=1[CH2:32][CH2:33][CH3:34]>CO>[Cl:3][C:4]1[C:13]2[C:8](=[C:9]([CH2:24][CH2:25][CH3:26])[C:10]3[O:17][C:16]([C:18]([OH:20])=[O:19])=[CH:15][C:14](=[O:23])[C:11]=3[CH:12]=2)[N:7]=[C:6]([C:27]([OH:29])=[O:28])[C:5]=1[CH2:32][CH2:33][CH3:34]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20478444HCID 20478444, compound

Product 1

HCID 13543945HCID 13543945, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.1 N Sodium hydroxide (28.9 mls) was added dropwise to the diester product of step (e) (0.646 g) in refluxing methanol (100 mls) with stirring, over 15 minutes. The reaction mixture was refluxed and stirred for a further 3 hours and the solution filtered and evaporated. The residue was dissolved in water (100 mls) and acidified. The precipitated acid was collected by filtration, washed with water and dried to give 0.4 g of the desired product. A recrystallisation from ethyl acetate gave 0.24 g, mp 204° (dec).

Workup

  1. temperatureThe reaction mixture was refluxed
  2. stirringstirred for a further 3 hours
  3. filtrationthe solution filtered
  4. customevaporated
  5. dissolutionThe residue was dissolved in water (100 mls)
  6. filtrationThe precipitated acid was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-f9c14759e28b44569ce76ce5f9059868
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

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