Acetic Acid → HCID 18972986, compound

HRID 2394310Notes

Reaction equation

HRID 2394310 reaction equation
[OH-].[Li+].O.[CH2:4]([N:11]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:12]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1)[C:13]([O:15]CC)=[O:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(O)(=O)C>C1COCC1>[CH2:4]([N:11]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:12]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1)[C:13]([OH:15])=[O:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 18972988HCID 18972988, compound

Product 1

HCID 18972986HCID 18972986, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (80 mg 1.8 mmol) and water (2 ml) were added to a solution of the product of step (c) (280 mg, 0.6 mmol) in THF (5 ml) and the mixture was stirred at room temperature for 16 hours. Acetic acid (0.5 ml) was added and the mixture was partitioned between ethyl acetate and water. The organic layer was dried (Na2SO4) and the solvent was evaporated under reduced pressure to give the title compound as a colourless foam (234 mg) m/e (CI+) 438 (MH+).

Workup

  1. customthe mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e0111ff76d89430d8351a8d019a1a033
Source dataset
uspto-grants-1998_09
Patent number
US05811431

Reaction notes

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