Potassium Carbonate → HCID 11377002, compound

HRID 490146Notes

Reaction equation

HRID 490146 reaction equation
[F:1][C@H:2]1[CH2:6][N:5]([C:7]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([CH3:16])[CH:14]=3)[NH:9][C:8]2=[O:17])[C@H:4]([C:26]([N:28]([CH3:30])[CH3:29])=[O:27])[CH2:3]1.[H-].[Na+].[CH3:33][O:34][C:35]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:36]=1[S:43](Cl)(=[O:45])=[O:44].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.CN(C)C=O>[CH3:33][O:34][C:35]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:36]=1[S:43]([N:9]1[C:10]2[C:15](=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[C:7]([N:5]2[CH2:6][C@H:2]([F:1])[CH2:3][C@H:4]2[C:26]([N:28]([CH3:30])[CH3:29])=[O:27])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])[C:8]1=[O:17])(=[O:44])=[O:45]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 27346262,4-Dimethoxybenzenesulfonyl chlorideHCID 67428853HCID 67428853, compound

Product 1

HCID 11377002HCID 11377002, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

620 mg of the compound obtained in step 15-1 (diastereoisomer mixture) was added under ice cooling and a nitrogen atmosphere to a 10 mL N,N-dimethylformamide solution of 67 mg of sodium hydride, and the reaction mixture was stirred for 40 minutes. After this, a 2 mL N,N-dimethylformamide solution of 400 mg of 2,4-dimethoxybenzenesulfonyl chloride was added dropwise. The reaction mixture was stirred for 30 minutes at the same temperature, after which 5 mL of ethyl acetate and 10 mL of a 5% potassium carbonate aqueous solution were added, and the reaction mixture was stirred at room temperature overnight. The precipitated solids were filtered off and separated and purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/acetone=99/1; v/v) to obtain two kinds of diastereoisomer of the titled compound in amounts of 184 mg (isomer A: colorless, amorphous) and 256 mg (isomer B: colorless, amorphous).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. filtrationThe precipitated solids were filtered off
  3. customseparated
  4. custompurified by column chromatography (silica gel 60, mobile phase: ethyl acetate/acetone=99/1; v/v)

Sources & evidence

ORD record
ord-1aefe5f7a75944018b9b6c3b0fb6ce39
Source dataset
uspto-grants-2009_05
Patent number
US07528124B2

Reaction notes

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