Sodium Hydroxide → (5-{2-[4-(5-Bromo-2-chlorophenoxy)piperidin-1-yl]pyrimidin-5-yl}-2H-tetrazol-2-yl)acetic acid

HRID 729463Notes

Reaction equation

HRID 729463 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:32])=[C:6]([CH:31]=1)[O:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][C:17]([C:20]3[N:21]=[N:22][N:23]([CH2:25][C:26]([O:28]CC)=[O:27])[N:24]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1.[OH-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:32])=[C:6]([CH:31]=1)[O:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[CH:16][C:17]([C:20]3[N:21]=[N:22][N:23]([CH2:25][C:26]([OH:28])=[O:27])[N:24]=3)=[CH:18][N:19]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86621802Ethyl (5-{2-[4-(5-bromo-2-chlorophenoxy)piperidin-1-yl]pyrimidin-5-yl}-2H-tetrazol-2-yl)acetate

Product 1

HCID 57518494(5-{2-[4-(5-Bromo-2-chlorophenoxy)piperidin-1-yl]pyrimidin-5-yl}-2H-tetrazol-2-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the ethyl (5-{2-[4-(5-bromo-2-chlorophenoxy)piperidin-1-yl]pyrimidin-5-yl}-2H-tetrazol-2-yl)acetate (50 mg, 0.096 mmol) in THF (319 μL) and MeOH (159 μL) was added 2 N NaOH (96 μL, 0.191 mmol) and the was mixture stirred at RT for 10 min. The THF and MeOH were evaporated and the aqueous layer was washed with Et2O (2×2 mL). The aqueous layer was acidified to pH 1 with 2 N HCl and stirred for 5 min. The mixture was filtered and washed with water followed by 1:1 Et2O/hexanes. The solid was dried under high vacuum to afford the title compound.

Workup

  1. customThe THF and MeOH were evaporated
  2. washthe aqueous layer was washed with Et2O (2×2 mL)
  3. stirringstirred for 5 min
  4. filtrationThe mixture was filtered
  5. washwashed with water
  6. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-6288b0432c4a4c188df10d894bcf446d
Source dataset
uspto-grants-2009_09
Patent number
US07582633B2

Reaction notes

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