Methanol → HCID 68304202, compound

HRID 1846685Notes

Reaction equation

HRID 1846685 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]([S:28]([CH3:31])(=[O:30])=[O: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[CH2:10][CH2:11][CH:6]([CH2:5][C:4]([OH:32])=[O:3])[CH2:7][CH2:8]2)=[N:13][C:14]([S:28]([CH3:31])(=[O:29])=[O:30])=[CH:15][CH:16]=1)=[O:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68304201HCID 68304201, compound

Product 1

HCID 68304202HCID 68304202, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 0.055 g (0.11 mmol) of [3′-(3-chloro-benzoylamino)-6′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid ethyl ester in a 2:1 mixture of tetrahydrofuran:methanol (6 mL) is added 0.014 g (0.57 mmol) of lithium hydroxide as a solution in water (1 mL). The mixture is stirred overnight at room temperature 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 0.023 g (44%) of [3′-(3-chloro-benzoylamino)-6′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid as a yellow 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-7122d7ddaf524c5285653a8fd345e8c0
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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