Water → 2-[2-(4-Acetamido-phenyl)-3-methyl-1-propyl-1H-indole-5-yloxy]-2-methyl-propanoic acid ethylester

HRID 66899Notes

Reaction equation

HRID 66899 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[C:5]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][CH2:19][CH3:20])[C:13]([C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)=[C:12]2[CH3:28])([CH3:7])[CH3:6])[CH3:2].C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38].O>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:29])[C:5]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][CH2:19][CH3:20])[C:13]([C:21]1[CH:22]=[CH:23][C:24]([NH:27][C:37](=[O:39])[CH3:38])=[CH:25][CH:26]=1)=[C:12]2[CH3:28])([CH3:6])[CH3:7])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 538662912-[2-(4-amino-phenyl)-3-methyl-1-propyl-1H-indole-5-yloxy]-2-methyl-propanoic acid ethylester

Product 1

HCID 537871562-[2-(4-Acetamido-phenyl)-3-methyl-1-propyl-1H-indole-5-yloxy]-2-methyl-propanoic acid ethylester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

One gram (2.53 m mole) of 2-[2-(4-amino-phenyl)-3-methyl-1-propyl-1H-indole-5-yloxy]-2-methyl-propanoic acid ethylester and 0.25 g (2.5 m mole) of triethylamine were dissolved in 15 ml of chloroform and 0.2 g (2.55 m mole) of acetyl chloride were added dropwise while ice-cooling. After a few hours at room temperature the reaction mixture was mixed with water and extracted with chloroform. The chloroform extracts were dried and evaporated, and the residue was purified by chromatography on silicagel (solvent: toluene/acetone (5:1)).

Workup

  1. temperaturecooling
  2. extractionextracted with chloroform
  3. dry with materialThe chloroform extracts were dried
  4. customevaporated
  5. customthe residue was purified by chromatography on silicagel (solvent: toluene/acetone (5:1))

Sources & evidence

ORD record
ord-edf9e13b99db4fcbb578d2343b4e2b70
Source dataset
uspto-grants-1982_08
Patent number
US04343811

Reaction notes

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