Potassium Carbonate → HCID 23157291, compound

HRID 508108Notes

Reaction equation

HRID 508108 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:21][C:22]2[CH:23]=[C:24]([C:32]3[C:37]([CH3:38])=[CH:36][C:35]([OH:39])=[CH:34][C:33]=3[CH3:40])[C:25]([O:28][CH:29]([CH3:31])[CH3:30])=[CH:26][CH:27]=2)[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])(=[O:11])=[O:10])[CH:5]=[CH:4][C:3]=1[CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44].[O:48]1[C:50]2([CH2:55][CH2:54][S:53][CH2:52][CH2:51]2)[CH2:49]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cl-].[Na+].O>[F:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:21][C:22]2[CH:23]=[C:24]([C:32]3[C:37]([CH3:38])=[CH:36][C:35]([O:39][CH2:49][C:50]4([OH:48])[CH2:55][CH2:54][S:53][CH2:52][CH2:51]4)=[CH:34][C:33]=3[CH3:40])[C:25]([O:28][CH:29]([CH3:31])[CH3:30])=[CH:26][CH:27]=2)[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])(=[O:11])=[O:10])[CH:5]=[CH:4][C:3]=1[CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 187531011-Oxa-6-thiaspiro(2.5)octaneHCID 23157334HCID 23157334, compound

Product 1

HCID 23157291HCID 23157291, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 3-(2-fluoro-4-{[(4′-hydroxy-6-isopropoxy-2′,6′-dimethylbiphenyl-3-yl)methyl][(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (993 mg, 1.49 mmol) and 1-oxa-6-thiaspiro[2.5]octane (779 mg, 5.98 mmol) in N,N-dimethylformamide (10 mL) was added potassium carbonate (827 mg, 5.98 mmol), and the mixture was stirred overnight at 80° C. Brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/1) to give the title compound (605 mg, yield 51%) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-0d9c8366936d421cb1d46147dbacefa6
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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