Potassium Carbonate → HCID 11262245, compound

HRID 490150Notes

Reaction equation

HRID 490150 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]3([N:21]4[CH2:30][C@H:29]([F:31])[CH2:28][C@H:22]4[C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([Cl:19])[CH:17]=4)[NH:12][C:11]3=[O:20])[C:4]=2[O:3][CH2:2]1.[H-].[Na+].[CH3:34][O:35][C:36]1[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:37]=1[S:44](Cl)(=[O:46])=[O:45].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]3([N:21]4[CH2:30][C@H:29]([F:31])[CH2:28][C@H:22]4[C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([Cl:19])[CH:17]=4)[N:12]([S:44]([C:37]4[CH:38]=[CH:39][C:40]([O:42][CH3:43])=[CH:41][C:36]=4[O:35][CH3:34])(=[O:46])=[O:45])[C:11]3=[O:20])[C:4]=2[O:3][CH2:2]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 27346262,4-Dimethoxybenzenesulfonyl chlorideHCID 67429478HCID 67429478, compound

Product 1

HCID 11262245HCID 11262245, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

353 mg of the compound obtained in step 18-1 (mixture of diastereoisomers) was added under ice cooling and a nitrogen atmosphere to a suspension of 35 mg of sodium hydride in 3 mL of tetrahydrofuran, and the reaction mixture was stirred for 20 minutes. After this, a 2 mL tetrahydrofuran solution of 219 mg of 2,4-dimethoxybenzenesulfonyl chloride was added dropwise. The reaction mixture was stirred for 2 hours 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 for 30 minutes at room temperature. After liquid separation, the aqueous layer was extracted with ethyl acetate (10 mL×3), and the combined organic layer was dried with sodium sulfate, after which the drying agent was filtered off and the solvent was distilled off under reduced pressure. The residue thus obtained was separated and purified by column chromatography (silica gel 60, mobile phase: ethyl acetate) to obtain two kinds of diastereoisomer of the titled compound in amounts of 191 mg (isomer A: colorless, amorphous) and 75 mg (isomer B: colorless, amorphous).

Workup

  1. stirringThe reaction mixture was stirred for 2 hours at the same temperature
  2. stirringthe reaction mixture was stirred for 30 minutes at room temperature
  3. customAfter liquid separation
  4. extractionthe aqueous layer was extracted with ethyl acetate (10 mL×3)
  5. dry with materialthe combined organic layer was dried with sodium sulfate
  6. filtrationafter which the drying agent was filtered off
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue thus obtained
  9. customwas separated
  10. custompurified by column chromatography (silica gel 60, mobile phase: ethyl acetate)

Sources & evidence

ORD record
ord-e69443d9eb3e4f8cb2794ed9ae0a9f5e
Source dataset
uspto-grants-2009_05
Patent number
US07528124B2

Reaction notes

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