Acetic Acid → HCID 178480318, compound

HRID 352687Notes

Reaction equation

HRID 352687 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[CH2:24][CH2:23][CH2:22][N:21]3[CH3:25])=[CH:16][N:15]=2)[CH2:7][CH2:6]1)=[O:4].[OH-].[K+].CC(O)=O>CO>[CH3:25][N:21]1[CH2:22][CH2:23][CH2:24][C@H:20]1[C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][CH2:11][C@H:8]2[CH2:7][CH2:6][C@H:5]([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]2)=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 178501083HCID 178501083, compound

Product 1

HCID 178480318HCID 178480318, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6 (0.11 g, 0.3 mmol) and KOH (0.025 g, 0.45 mmol) in 50% aqueous MeOH (10 mL) was heated under reflux for 30 min. The reaction mixture was acidified with HOAc to pH 8 and the solvents were evaporated in vacuo. The crude product was purified by column chromatography (silica gel, CHCl3/MeOH, gradient of MeOH 10% to 50%) to afford 0.077 g (74%) of 7.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 min
  3. customthe solvents were evaporated in vacuo
  4. customThe crude product was purified by column chromatography (silica gel, CHCl3/MeOH, gradient of MeOH 10% to 50%)

Sources & evidence

ORD record
ord-0fb7ccec278d4544a8c3daf5ee38c490
Source dataset
uspto-grants-2004_06
Patent number
US06747156B2

Reaction notes

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