Methanol → HCID 68304439, compound

HRID 1846680Notes

Reaction equation

HRID 1846680 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:17]([NH:18][C:19](=[O:27])[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)=[CH:16][CH:15]=[C:14]([C:28]([F:31])([F:30])[F:29])[N:13]=2)[CH2:8][CH2:7]1)C.O1CCCC1.CO.[OH-].[Li+]>O>[Cl:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[C:19]([NH:18][C:17]1[C:12]([N:9]2[CH2:8][CH2:7][CH:6]([CH2:5][C:4]([OH:32])=[O:3])[CH2:11][CH2:10]2)=[N:13][C:14]([C:28]([F:30])([F:29])[F:31])=[CH:15][CH:16]=1)=[O:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68304437HCID 68304437, compound

Product 1

HCID 68304439HCID 68304439, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 0.230 g (0.489 mmol) of [3′-(3-chloro-benzoylamino)-6′-trifluoromethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid ethyl ester in a 2:1 mixture of tetrahydrofuran:methanol (12 mL) is added 0.058 g (2.4 mmol) of lithium hydroxide as a solution in water (2 mL). The mixture is stirred at room temperature for 2 hours then concentrated under reduced pressure. The residue is diluted with water and the pH of the mixture is adjusted to pH 2 by the addition of concentrated hydrochloric acid causing a solid to precipitate from solution. The formed precipitate is collected by filtration and dried to provide 0.21 g (quant) of [3′-(3-chloro-benzoylamino)-6′-trifluoromethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid as a white solid.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. additionThe residue is diluted with water
  3. additionthe pH of the mixture is adjusted to pH 2 by the addition of concentrated hydrochloric acid causing a solid
  4. customto precipitate from solution
  5. filtrationThe formed precipitate is collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-a091fd675d474a05b2b0b35be7ea6184
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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