Potassium Iodide → HCID 11250901, compound

HRID 1181600Notes

Reaction equation

HRID 1181600 reaction equation
[C:1](=[O:13])([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[O:2][CH:3](Cl)[CH3:4].[OH:14][C@H:15]([CH2:35][NH:36][C:37]([CH3:50])([CH3:49])[CH2:38][C:39]1[CH:48]=[CH:47][C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=1)[CH2:16][O:17][CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[CH:31]=[CH:30][C:29]([C:32]([OH:34])=[O:33])=[CH:28][CH:27]=1)[CH3:19].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.O>[OH:14][C@H:15]([CH2:35][NH:36][C:37]([CH3:49])([CH3:50])[CH2:38][C:39]1[CH:48]=[CH:47][C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=1)[CH2:16][O:17][CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[CH:27]=[CH:28][C:29]([C:32]([O:34][CH:3]([O:2][C:1]([O:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[O:13])[CH3:4])=[O:33])=[CH:30][CH:31]=1)[CH3:19]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 112295291-Chloroethyl Cyclohexyl CarbonateHCID 53318971HCID 53318971, compound

Product 1

HCID 11250901HCID 11250901, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1-Chloroethyl cyclohexyl carbonate (149 mg) obtained in Step 1 was dissolved in N,N-dimethylformamide (5.0 ml), 2′-[1-[(2R)-2-hydroxy-3-[[2-methyl-1-(naphthalen-2-yl)propan-2-yl]amino]propoxy]ethyl]biphenyl-4-carboxylic acid (300 mg) obtained in Step 2, potassium carbonate (99 mg) and potassium iodide (50 mg) were successively added and the mixture was stirred at 60° C. for 1 day. Water was added to the reaction mixture and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed successively with water (3 times) and brine, and dried over sodium sulfate. The organic layer was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=15:1) to give the title compound (381 mg).

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. washThe organic layer was washed successively with water (3 times) and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-9547b7c4697a4b7fbda275060e9b63bd
Source dataset
uspto-grants-2007_10
Patent number
US07285572B2

Reaction notes

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