Methanol → HCID 68304342, compound

HRID 1846647Notes

Reaction equation

HRID 1846647 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](=[O:33])[NH:29][CH:30]3[CH2:32][CH2:31]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](=[O:33])[NH:29][CH:30]2[CH2:31][CH2:32]2)[CH:16]=1)=[O:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68304348HCID 68304348, compound

Product 1

HCID 68304342HCID 68304342, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.23 g (0.47 mmol) of [3′-(3-chloro-benzoylamino)-5′-cyclopropylcarbamoyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid ethyl ester in a 5:2 mixture of tetrahydrofuran:methanol is added a solution of 0.056 g (2.3 mmol) of lithium hydroxide in water (1 mL). The reaction mixture is stirred overnight and then concentrated under reduced pressure to remove volatile organics. 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 colorless solid is collected by filtration and dried under vacuum to provide 0.14 g (66%) of [3′-(3-chloro-benzoylamino)-5′-cyclopropylcarbamoyl-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 pH of the mixture is adjusted to approximately pH 2 by the addition of concentrated hydrochloric acid causing a solid
  4. customto precipitate
  5. filtrationThe formed colorless solid is collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-6b48736e6eb049b6b2c3d6aefc9bcdd6
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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