Water → HCID 23124677, compound

HRID 2357764Notes

Reaction equation

HRID 2357764 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][N:10]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[C:9]2[CH:18]=[CH:19][CH:20]=[C:21](/[CH:22]=[CH:23]/[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:26][CH:25]=3)[C:8]=2[O:7]1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:47](I)[CH3:48].O>CN(C)C=O>[CH2:47]([O:16][C:15](=[O:17])[CH2:14][CH2:13][CH2:12][N:10]1[C:9]2[CH:18]=[CH:19][CH:20]=[C:21](/[CH:22]=[CH:23]/[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[CH:26][CH:25]=3)[C:8]=2[O:7][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11]1)[CH3:48]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 23124586HCID 23124586, compound

Product 1

HCID 23124677HCID 23124677, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound prepared in Example 46 (330 mg) in dimethylformamide (5 mL) were added potassium carbonate (252 mg) and ethyl iodide (142 mg), and the mixture was stirred for 2 hours at room temperature. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine sequentially, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=8:2) to give the title compound (210 mg) having the following physical data.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine sequentially
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-3f6a60bacbec4a9cbb1c6e63031a23a2
Source dataset
uspto-grants-2010_07
Patent number
US07763610B2

Reaction notes

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