Methanol → HCID 68304426, compound

HRID 1846649Notes

Reaction equation

HRID 1846649 reaction equation
C([O:3][C:4](=[O:34])[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][C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:14][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:34])=[O:3])[CH2:7][CH2:8]2)=[N:13][CH:14]=[C:15]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:16]=1)=[O:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68304427HCID 68304427, compound

Product 1

HCID 68304426HCID 68304426, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.115 g (0.241 mmol) of [3′-(3-chloro-benzoylamino)-5′-phenyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid ethyl ester in a 5:2 mixture of tetrahydrofuran:methanol (7 mL) is added a solution of 0.028 g (1.2 mmol) of lithium hydroxide in water (1 mL). The reaction mixture is stirred at room temperature for 3 days and then concentrated under reduced pressure to remove volatile organics. The residue is diluted with water and the pH of the mixture is adjusted to approximately pH 2 by the addition of concentrated hydrochloric acid causing a solid to precipitate. The formed yellow solid is collected by filtration and dried under vacuum to provide 0.090 g (83%) of [3′-(3-chloro-benzoylamino)-5′-phenyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove volatile organics
  3. additionThe residue is diluted with water
  4. additionthe pH of the mixture is adjusted to approximately pH 2 by the addition of concentrated hydrochloric acid causing a solid
  5. customto precipitate
  6. filtrationThe formed yellow solid is collected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-3537345d43d846f2a2dd0bf6c9925afb
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

Loading…