Potassium Carbonate → HCID 11490882, compound

HRID 490148Notes

Reaction equation

HRID 490148 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([N:22]1[CH2:31][C@H:30]([F:32])[CH2:29][C@H:23]1[C:24]([N:26]([CH3:28])[CH3:27])=[O:25])([C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=1[O:20][CH3:21])[C:5](=[O:12])[NH:6]2.[H-].[Na+].[CH3:35][O:36][C:37]1[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:38]=1[S:45](Cl)(=[O:47])=[O:46].C(=O)([O-])[O-].[K+].[K+]>C(OC(=O)C)C.O1CCCC1>[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([N:22]1[CH2:31][C@H:30]([F:32])[CH2:29][C@H:23]1[C:24]([N:26]([CH3:28])[CH3:27])=[O:25])([C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=1[O:20][CH3:21])[C:5](=[O:12])[N:6]2[S:45]([C:38]1[CH:39]=[CH:40][C:41]([O:43][CH3:44])=[CH:42][C:37]=1[O:36][CH3:35])(=[O:47])=[O:46]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 27346262,4-Dimethoxybenzenesulfonyl chlorideHCID 67430977HCID 67430977, compound

Product 1

HCID 11490882HCID 11490882, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

301 mg of the compound obtained in step 16-2 (diastereoisomer mixture) was added under ice cooling and a nitrogen atmosphere to a 3 mL tetrahydrofuran solution of 26 mg of sodium hydride, and the reaction mixture was stirred for 20 minutes. After this, a 2 mL tetrahydrofuran solution of 170 mg of 2,4-dimethoxybenzenesulfonyl chloride was added dropwise, and the reaction mixture was stirred for 2 hours at room temperature. Then 5 mL of ethylacetate 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/acetone=99/1; v/v) to obtain two kinds of diastereoisomer of the titled compound in amounts of 115 mg (isomer A: colorless, amorphous) and 127 mg (isomer B: colorless, amorphous).

Workup

  1. stirringthe reaction mixture was stirred for 30 minutes at room temperature
  2. customAfter liquid separation
  3. extractionthe aqueous layer was extracted with ethyl acetate (10 mL×3)
  4. dry with materialthe combined organic layer was dried with sodium sulfate
  5. filtrationafter which the drying agent was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue thus obtained
  8. customwas separated
  9. custompurified by column chromatography (silica gel 60, mobile phase: ethyl acetate/acetone=99/1; v/v)

Sources & evidence

ORD record
ord-1a1f8fad853a447384b780a28a01abea
Source dataset
uspto-grants-2009_05
Patent number
US07528124B2

Reaction notes

Loading…