Sodium Bicarbonate → HCID 22033010, compound

HRID 1792341Notes

Reaction equation

HRID 1792341 reaction equation
COC[O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:26][CH2:27][CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][S:39][CH2:40][CH2:41][CH2:42][C:43]([F:49])([F:48])[C:44]([F:47])([F:46])[F:45])=[CH:32][CH:31]=3)[C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22]COC)=[CH:18][CH:17]=3)([CH3:15])[CH2:11][S:12]2)=[CH:7][CH:6]=1.C(=O)([O-])O.[Na+]>Cl.CO.O1CCCC1>[OH:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:26][CH2:27][CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][S:39][CH2:40][CH2:41][CH2:42][C:43]([F:49])([F:48])[C:44]([F:45])([F:46])[F:47])=[CH:32][CH:31]=3)[C:10]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)([CH3:15])[CH2:11][S:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 22033190HCID 22033190, compound

Product 1

HCID 22033010HCID 22033010, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21893726Hydrochloride methanolSolvent

Procedure

(3RS,4RS)-7-Methoxymethoxy-3-[4-(methoxymethoxy)phenyl]-3-methyl-4-{3-{4-[2-(4,4,5,5,5-pentafluoropentylthio)ethoxy]phenoxy}propyl}thiochroman (9) prepared in Step 7 (144 mg, 0.2 mmol) was dissolved in hydrochloric acid/methanol (1 ml) and tetrahydrofuran (0.1 ml), which was then stirred at room temperature for 4 days. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution, and the resulting mixture was extracted with ethyl acetate and chloroform. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and subjected to silica gel column chromatography to give (3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-{3-{4-[2-(4,4,5,5,5-pentafluoropentylthio)ethoxy]phenoxy}propyl}thiochroman (11) (110 mg, yield 87%) as a yellow oily substance.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate and chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-32aedadbaf564aa7aef1ae73987f1ae9
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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