Acetic Acid → HCID 11846909, compound

HRID 1172840Notes

Reaction equation

HRID 1172840 reaction equation
[Cl:1][C:2]1[C:27]([O:28][C@@H:29]([CH3:34])[C:30]([O:32]C)=[O:31])=[CH:26][C:5]2[C:6]([C:9]3[C:10]([CH2:23][CH2:24][CH3:25])=[N:11][C:12]([O:15][C:16]4[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=4)=[CH:13][CH:14]=3)=[N:7][O:8][C:4]=2[CH:3]=1.[OH-].[Na+].C(O)(=O)C>CO>[Cl:1][C:2]1[C:27]([O:28][C@@H:29]([CH3:34])[C:30]([OH:32])=[O:31])=[CH:26][C:5]2[C:6]([C:9]3[C:10]([CH2:23][CH2:24][CH3:25])=[N:11][C:12]([O:15][C:16]4[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=4)=[CH:13][CH:14]=3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 59556491HCID 59556491, compound

Product 1

HCID 11846909HCID 11846909, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The ester from Step 1 (2.3 g, 4.5 mmol) was dissolved in methanol (45 mL) and treated with 2 N NaOH (4.5 mL, 9.0 mmol) at room temperature for 1 h. The reaction mixture was acidified with acetic acid (2.0 mL) and methanol was removed under reduced pressure. The residue was taken up in ethyl acetate and the resulting solution was washed with brine and dried over MgSO4. After removal of the solvent, the crude acid was recrystallized in ether-hexane (1:10) to give the title product as a white solid.

Workup

  1. customwas removed under reduced pressure
  2. washthe resulting solution was washed with brine
  3. dry with materialdried over MgSO4
  4. customAfter removal of the solvent
  5. customthe crude acid was recrystallized in ether-hexane (1:10)

Sources & evidence

ORD record
ord-1ab8582a69564d0aba88702924ec98dd
Source dataset
uspto-grants-2010_11
Patent number
US07834036B2

Reaction notes

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