Isopropyl iodide → HCID 59428672, compound

HRID 504149Notes

Reaction equation

HRID 504149 reaction equation
[CH:1](I)([CH3:3])[CH3:2].[CH2:5]([O:12][C:13](=[O:42])[C@@H:14]([NH:23][C:24]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][N:27]1[S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=1)(=[O:34])=[O:33])=[O:25])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:5]([O:12][C:13](=[O:42])[C@@H:14]([NH:23][C:24]([C@@H:26]1[CH2:31][CH2:30][CH2:29][CH2:28][N:27]1[S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=1)(=[O:34])=[O:33])=[O:25])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH:1]([CH3:3])[CH3:2])=[CH:18][CH:17]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 66750780HCID 66750780, compound

Product 1

HCID 59428672HCID 59428672, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Isopropyl iodide (0.62 mL, 6.2 mmol) was added to a mixture of (S)-2-{[1-(3-(fluoro)-benzenesulfonyl)-piperidine-2-carbonyl]-amino}-3-(4-hydroxy-phenyl)-propionic acid benzyl ester (700 mg, 1.30 mmol) and cesium carbonate (2.4 g, 7.4 mmol) in dry DMF (5 mL). The suspension was stirred at room temperature for 4 h. The reaction mixture was then washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The resulting oil was chromatographed (ethyl acetate/n-heptane) on silica gel to produce 620 mg (82.1%) of the title compound.

Workup

  1. washThe reaction mixture was then washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting oil was chromatographed (ethyl acetate/n-heptane) on silica gel

Sources & evidence

ORD record
ord-27c2c4f64f3c4187919d39318bd13073
Source dataset
uspto-grants-2010_08
Patent number
US07777042B2

Reaction notes

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