Hydrochloric Acid → 2-((S)-6-((R)-4-(2,6-Dimethyl-4-(pyrimidin-5-yl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

HRID 237705Notes

Reaction equation

HRID 237705 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[N:14][CH:15]=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)(=O)C.O1CCOCC1>[CH3:3][C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[N:14][CH:15]=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]([OH:38])=[O:37])[CH2:33][O:34][C:30]=2[CH:29]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86697133Methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(pyrimidin-5-yl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 866973742-((S)-6-((R)-4-(2,6-Dimethyl-4-(pyrimidin-5-yl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

1 M aqueous NaOH solution (167 μL) is added to a solution of methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(pyrimidin-5-yl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (35 mg) in methanol (3 mL). The mixture is stirred at 40° C. for 1 hour. After addition of 1 N hydrochloric acid (167 μL) the mixture is diluted with ethyl acetate and washed with brine. The organic phase is dried (MgSO4) and concentrated. The product thus obtained is dissolved in 1,4-dioxane and lyophilized to give the title compound. Yield: 29 mg; LC (method 11): tR=1.14 min; Mass spectrum (ESI+): m/z=511 [M+H]+.

Workup

  1. washwashed with brine
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated
  4. customThe product thus obtained

Sources & evidence

ORD record
ord-33e6e0c1197943e584928294fa51bc26
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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