Acetic Acid → HCID 19737283, compound

HRID 258477Notes

Reaction equation

HRID 258477 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][CH:12]([S:32][CH2:33][CH:34]([CH3:40])[C:35]([O:37]CC)=[O:36])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][C:25]([Cl:31])=[CH:26][CH:27]=3)[N:22]=2)[CH:14]=1)(=[O:3])[CH3:2].[OH-].[Na+].CC(O)=O>CO.C1COCC1>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][CH:12]([S:32][CH2:33][CH:34]([CH3:40])[C:35]([OH:37])=[O:36])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][C:25]([Cl:31])=[CH:26][CH:27]=3)[N:22]=2)[CH:14]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 19737253HCID 19737253, compound

Product 1

HCID 19737283HCID 19737283, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of the ester of Step 7 (3.844 g, 6.67 mmol) and 1.0N NaOH (13 mL) in 55 mL of MeOH:THF 3:2 was stirred at r.t. for 24 h. 25% Aq NH4OAc was then added and the mixture was acidified with AcOH. The title acid was extracted with EtOAc, dried over Na2SO4 and purified by flash chromatography on silica with acetone:toluene:AcOH 5:95:1. Yield 3.491 g, 95%.

Workup

  1. extractionThe title acid was extracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. custompurified by flash chromatography on silica with acetone:toluene:AcOH 5:95:1

Sources & evidence

ORD record
ord-418c3d58ca3148c7aca7876114cd28fb
Source dataset
uspto-grants-1993_11
Patent number
US05266568

Reaction notes

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