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Hydrochloric Acid → 2-((S)-6-((R)-4-(2,6-Dimethyl-4-((S)-tetrahydrofuran-3-yloxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

HRID 237701
Notes
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Reaction equation

HRID 237701 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([O:10][C@H:11]2[CH2:15][CH2:14][O:13][CH2:12]2)[CH:7]=[C:6]([CH3:16])[C:5]=1[C:17]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]2[C:18]=1[CH2:19][CH2:20][C@H:21]2[O:27][C:28]1[CH:41]=[CH:40][C:31]2[C@H:32]([CH2:35][C:36]([O:38]C)=[O:37])[CH2:33][O:34][C:30]=2[CH:29]=1.Cl>CO.C(OCC)C.C(#N)C.O>[CH3:16][C:6]1[CH:7]=[C:8]([O:10][C@H:11]2[CH2:15][CH2:14][O:13][CH2:12]2)[CH:9]=[C:4]([CH3:3])[C:5]=1[C:17]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]2[C:18]=1[CH2:19][CH2:20][C@H:21]2[O:27][C:28]1[CH:41]=[CH:40][C:31]2[C@H:32]([CH2:35][C:36]([OH:38])=[O:37])[CH2:33][O:34][C:30]=2[CH:29]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86697117Methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-((S)-tetrahydrofuran-3-yloxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 717378982-((S)-6-((R)-4-(2,6-Dimethyl-4-((S)-tetrahydrofuran-3-yloxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

Reagents, catalysts & solvents

3
HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
40 °C

Procedure

1 M aqueous NaOH solution (585 μL) is added to a solution of methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-((S)-tetrahydrofuran-3-yloxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (125 mg) in methanol (3 mL). The mixture is stirred at 40° C. for 12 hours. After addition of 1 N hydrochloric acid (585 μL) the mixture is diluted with diethylether and washed with water and brine. The organic phase is dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30→20:80). The product thus obtained is dissolved in acetonitrile/water (1:1) and lyophilized to give the title compound. Yield: 55 mg; LC (method 4): tR=1.82 min; Mass spectrum (ESI+): m/z=519 [M+H]+.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic phase is dried (MgSO4)
  3. customThe solvent is evaporated
  4. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30→20:80)
  5. customThe product thus obtained

Sources & evidence

ORD record
ord-2ac994ac66c74fbca6976755de22bf57
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08642585B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes