Water → HCID 68304433, compound

HRID 1846669Notes

Reaction equation

HRID 1846669 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[NH:19][C:20](=[O:28])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[CH2:8][CH2:7]1)C.O.[OH-].[Li+]>O1CCCC1.CO>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([N:9]2[CH2:10][CH2:11][CH:6]([CH2:5][C:4]([OH:29])=[O:3])[CH2:7][CH2:8]2)=[C:13]([NH:19][C:20](=[O:28])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 68304434HCID 68304434, compound

Product 1

HCID 68304433HCID 68304433, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.590 g (1.35 mmol) of {1-[4-chloro-2-(3-chloro-benzoylamino)-phenyl]-piperidin-4-yl}-acetic acid ethyl ester in a mixture of tetrahydrofuran (10 mL) and methanol (4 mL) is added water (2 mL) followed by 0.16 g (6.8 mmol) of lithium hydroxide. The mixture is stirred overnight at room temperature. The mixture is concentrated under reduced pressure to remove volatile organics and the pH of the resulting solution is adjusted to approximately pH 4 by the addition of concentrated hydrochloric acid. A green oil forms at the bottom of the mixture. The aqueous layer is removed by decanting and the green oil is concentrated under reduced pressure to provide 0.46 g (83%) of {1-[4-chloro-2-(3-chloro-benzoylamino)-phenyl]-piperidin-4-yl}-acetic acid as a green solid.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customto remove volatile organics
  3. additionthe pH of the resulting solution is adjusted to approximately pH 4 by the addition of concentrated hydrochloric acid
  4. customThe aqueous layer is removed
  5. customby decanting
  6. concentrationthe green oil is concentrated under reduced pressure

Sources & evidence

ORD record
ord-56d5a17b34174388a65fb2f4c85e0083
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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