Hexane → (3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylaminosulfonyl)nonyl]chroman

HRID 1792345Notes

Reaction equation

HRID 1792345 reaction equation
COC[O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][S:35]([NH:38][CH2:39][CH2:40][CH2:41][C:42]([F:48])([F:47])[C:43]([F:46])([F:45])[F:44])(=[O:37])=[O:36])[C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22]COC)=[CH:18][CH:17]=3)([CH3:15])[CH2:11][O:12]2)=[CH:7][CH:6]=1.C([O-])(O)=O.[Na+].CCCCCC.C(OCC)(=O)C>C1COCC1.C(O)(C)C.Cl>[OH:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][S:35]([NH:38][CH2:39][CH2:40][CH2:41][C:42]([F:47])([F:48])[C:43]([F:44])([F:45])[F:46])(=[O:36])=[O:37])[C:10]([C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)([CH3:15])[CH2:11][O:12]2)=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 220332707-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylaminosulfonyl)nonyl]chroman

Product 1

HCID 22033049(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylaminosulfonyl)nonyl]chromanYield 11.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

7-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylaminosulfonyl)nonyl]chroman (8.0 mg, 0.0113 mmol) was dissolved in a solvent mixture of THF (0.2 ml) and isopropanol (0.2 ml), 5N-HCl aqueous solution (0.6 ml) was added dropwise thereto, and the mixture was stirred at room temperature for 3 days. After the reaction was completed, the mixture was cooled, and then saturated aqueous NaHCO3 solution was added thereto. The resulting mixture was extracted with chloroform and washed with saturated saline solution. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give (3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylaminosulfonyl)nonyl]chroman (0.78 mg, yield 11%).

Workup

  1. additionwas added dropwise
  2. temperaturethe mixture was cooled
  3. extractionThe resulting mixture was extracted with chloroform
  4. washwashed with saturated saline solution
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained

Sources & evidence

ORD record
ord-fae7bc854963435c88c7067942589ab2
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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