Sodium Chloride → 1-[4-(Carboxymethoxy)benzyl]-3-dodecanoylindole-2-carboxylic acid

HRID 382828Notes

Reaction equation

HRID 382828 reaction equation
[C:1]([C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15]=1[C:23]([O:25]CC)=[O:24])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CC(C)([O-])C.Br[CH2:34][C:35]1[CH:47]=[CH:46][C:38]([O:39][CH2:40][C:41]([O:43]CC)=[O:42])=[CH:37][CH:36]=1.[Na+].[Cl-]>O.CS(C)=O>[C:41]([CH2:40][O:39][C:38]1[CH:46]=[CH:47][C:35]([CH2:34][N:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14]([C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[C:15]2[C:23]([OH:25])=[O:24])=[CH:36][CH:37]=1)([OH:43])=[O:42]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 45749132-Methylpropan-2-olateHCID 106192401H-Indole-2-carboxylic acid, 3-(1-oxododecyl)-, ethyl esterHCID 12870369Ethyl 2-[4-(bromomethyl)phenoxy]acetate

Product 1

HCID 183620641-[4-(Carboxymethoxy)benzyl]-3-dodecanoylindole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 223 mg (0.6 mmol) of ethyl 3-dodecanoylindole-2-carboxylate, 81 mg (0.72 mmol) of potasisum t-butoxide and 2 ml of absol. DMSO is stirred in an oil bath at 110° C. for 5 min. Then 197 mg (0.72 mmol) of ethyl 2-[4-(bromomethyl)phenoxy]acetate are added, and the mixture is heated at the same temperature for a further 10 min. Cooling and addition of water and NaCl are followed by extraction with ether. The organic phase is dried over Na2SO4, the solvent is distilled off, and the residue is chromato-graphed on silica gel with petroleum ether/ethyl acetate (9+1). The resulting ethyl 3-dodecanoyl-1-{4-[(ethoxycarbonyl)methoxy]benzyl}indole-2-carboxylate is hydrolyzed in analogy to Example 2E. The product is precipitated from ether.

Workup

  1. temperaturethe mixture is heated at the same temperature for a further 10 min
  2. temperatureCooling
  3. extractionare followed by extraction with ether
  4. dry with materialThe organic phase is dried over Na2SO4
  5. distillationthe solvent is distilled off
  6. customThe product is precipitated from ether

Sources & evidence

ORD record
ord-051fa19db58d463f85a8a8f8c2582f58
Source dataset
uspto-grants-2001_10
Patent number
US06310217B1

Reaction notes

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