Methanol → (4-{2-[(1S,2R)-2-{1-[5-(ethoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethoxy}-2-fluorophenyl)acetic acid

HRID 1474705Notes

Reaction equation

HRID 1474705 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([C@H:17]3[CH2:19][C@H:18]3[CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][C:30]([O:32]C)=[O:31])=[C:25]([F:34])[CH:24]=3)[CH2:13][CH2:12]2)=[N:9][CH:10]=1)[CH3:2].CO.[OH-].[Li+]>C1COCC1>[CH2:1]([O:3][CH2:4][C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:12][CH2:13][CH:14]([C@H:17]3[CH2:19][C@H:18]3[CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][C:30]([OH:32])=[O:31])=[C:25]([F:34])[CH:24]=3)[CH2:15][CH2:16]2)=[N:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 89583896Methyl (4-{2-[(1S,2R)-2-{1-[5-(ethoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethoxy}-2-fluorophenyl)acetate

Product 1

HCID 89582003(4-{2-[(1S,2R)-2-{1-[5-(ethoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethoxy}-2-fluorophenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl (4-{2-[(1S,2R)-2-{1-[5-(ethoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethoxy}-2-fluorophenyl)acetate (1.4 g, 2.97 mmol) was dissolved in THF (3 ml):MeOH (30 ml) and 1M lithium hydroxide (14.84 ml, 14.84 mmol) added. The mixture was stirred at RT overnight. The mixture was concentrated in vacuo and the residue diluted with water (5 mL). The pH of the solution was adjusted to pH˜5 by addition of 1N HCl and the aqueous phase was extracted with EtOAc (3×10 mL). The organic fractions were combined, washed with brine, dried over MgSO4 and concentrated under reduced pressure to afford the title compound. LC/MS (m/z): 458 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue diluted with water (5 mL)
  3. additionThe pH of the solution was adjusted to pH˜5 by addition of 1N HCl
  4. extractionthe aqueous phase was extracted with EtOAc (3×10 mL)
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-894090eea6d44192ae50201907d83998
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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