Hydrochloric Acid → 4-[(3R)-3-{[6-(2-Fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]oxy}piperidin-1-yl]butyric acid

HRID 2189125Notes

Reaction equation

HRID 2189125 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][C@@H:9]([O:13][C:14]2[C:15]3[C:22]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)=[C:21]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[F:37])[O:20][C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:8]1.[OH-].[Na+].Cl.C(OCC)(=O)C>O1CCOCC1>[F:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:21]1[O:20][C:16]2[N:17]=[CH:18][N:19]=[C:14]([O:13][C@@H:9]3[CH2:10][CH2:11][CH2:12][N:7]([CH2:6][CH2:5][CH2:4][C:3]([OH:38])=[O:2])[CH2:8]3)[C:15]=2[C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 582800764-[(3R)-3-{[6-(2-Fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]oxy}piperidin-1-yl]butyric acid methyl ester

Product 1

HCID 582801604-[(3R)-3-{[6-(2-Fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]oxy}piperidin-1-yl]butyric acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Dissolve 113 mg (0.20 mmol) of 4-[(3R)-3-{[6-(2-fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]-pyrimidin-4-yl]oxy}piperidin-1-yl]butyric acid methyl ester in 3 ml of dioxane and add 0.8 ml of a 1 N sodium hydroxide solution. Stir at room temperature for 16 hours, then add 0.8 ml of 1 N hydrochloric acid and 10 ml of ethyl acetate. Remove the organic phase, dry over sodium sulphate, filter and concentrate. 95 mg (90% of theory) of the target compound are obtained.

Workup

  1. customRemove the organic phase
  2. dry with materialdry over sodium sulphate
  3. filtrationfilter
  4. concentrationconcentrate
  5. custom95 mg (90% of theory) of the target compound are obtained

Sources & evidence

ORD record
ord-39547f145e37400b85b2b3d48a7094f4
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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