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Hydrochloric Acid → 10-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)thiochroman-4-yl]-2-(7,7,8,8,8-pentafluoro-octyl)decanoic acid

HRID 1267758
Notes
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Reaction equation

HRID 1267758 reaction equation
[OH-].[Na+].[CH2:3]([C:5]1([C:43]2[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=2)[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([F:41])([F:40])[C:36]([F:39])([F:38])[F:37])[C:24]([O:26]CC)=[O:25])[C:13]2[C:8](=[CH:9][C:10]([OH:42])=[CH:11][CH:12]=2)[S:7][CH2:6]1)[CH3:4].Cl>O.C(O)C>[CH2:3]([C:5]1([C:43]2[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=2)[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([F:41])([F:40])[C:36]([F:38])([F:37])[F:39])[C:24]([OH:26])=[O:25])[C:13]2[C:8](=[CH:9][C:10]([OH:42])=[CH:11][CH:12]=2)[S:7][CH2:6]1)[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18546284ethyl 10-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)thiochroman-4-yl]-2-(7,7,8,8,8-pentafluorooctyl)decanoate

Product 1

HCID 1854627710-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)thiochroman-4-yl]-2-(7,7,8,8,8-pentafluoro-octyl)decanoic acidYield 89.9%

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (325 mg) in water (4 ml) was added to a solution of ethyl 10-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)thiochroman-4-yl]-2-(7,7,8,8,8-pentafluorooctyl)decanoate (558 mg, 0.81 mmol) in ethanol (8 ml). The reaction mixture was heated under reflux for 12 hours. Dilute hydrochloric acid was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=2/1) to give 10-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)thiochroman-4-yl]-2-(7,7,8,8,8-pentafluoro-octyl)decanoic acid (480 mg, Yield 89%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 12 hours
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent
  7. customthe residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-2daaf73188364408b63e2c39e3fc98fe
Source dataset
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06552068B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes