HCID 54523819, compound → HCID 53678456, compound

HRID 2119843Notes

Reaction equation

HRID 2119843 reaction equation
[OH:1][C@@H:2]([CH2:18][N:19]([C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([O:39]CC)=[O:38])=[CH:33][C:32]=2[I:42])=[CH:26][CH:25]=1)[CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:3][O:4][C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1>C(O)C.[OH-].[K+].O>[OH:1][C@@H:2]([CH2:18][N:19]([C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([OH:39])=[O:38])=[CH:33][C:32]=2[I:42])=[CH:26][CH:25]=1)[CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:3][O:4][C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 1

HCID 54523819HCID 54523819, compound

Product 1

HCID 53678456HCID 53678456, compoundYield 105.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

(S)-4-[2-hydroxy-3-([4-(4-carboethoxy-2-iodophenoxy)phenyl]-2-methylpropylamino)propoxy]carbazole (386 mg, 0.54 mmol) was dissolved in a mixture of ethanol (20 ml) and aqueous potassium hydroxide (20 ml, 5.ON) and was stirred at ambient temperature for 16 hours. The crude reaction mixture was concentrated in vacuo and the residue acidified with 5.0N HCl. The solution was allowed to stir for one hour at 0° C. and then concentrated in vacuo to afford a white solid. The residue was suspended in water and filtered, and the solids washed with cold water. The solids were triturated with pentane and dried to afford product as a white solid (370 mg, 100%). NMR, MS, IR, HPLC

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo
  3. stirringto stir for one hour at 0° C.
  4. concentrationconcentrated in vacuo
  5. customto afford a white solid
  6. filtrationfiltered
  7. washthe solids washed with cold water
  8. customThe solids were triturated with pentane
  9. customdried

Sources & evidence

ORD record
ord-1add798e554c41ee9cb1d258a05c4f27
Source dataset
uspto-grants-2004_02
Patent number
US06686372B2

Reaction notes

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