Water → HCID 68304432, compound

HRID 1846661Notes

Reaction equation

HRID 1846661 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][C:15]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:14][N:13]=2)[CH2:8][CH2:7]1)C.O.[OH-].[Na+]>CO>[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][CH:14]=[C:15]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:16]=1)=[O:27]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68303804HCID 68303804, compound

Product 1

HCID 68304432HCID 68304432, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 1.41 g (2.94 mmol) of [3′-(3-Chloro-benzoylamino)-5′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid ethyl ester in a 1:1 mixture of water:methanol (30 mL) is added 4.0 mL (10 mmol) of sodium hydroxide as a 10% aqueous solution. After stirring at room temperature overnight the methanol is removed under reduced pressure and the pH of the resulting solution is adjusted to approximately pH 5 by the addition of a 2 N solution of hydrochloric acid. The mixture is extracted with ethyl acetate and the combined organic phase is dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide 1.10 g (82.9%) of [3′-(3-chloro-benzoylamino)-5′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid as an orange oil.

Workup

  1. customis removed under reduced pressure
  2. additionthe pH of the resulting solution is adjusted to approximately pH 5 by the addition of a 2 N solution of hydrochloric acid
  3. extractionThe mixture is extracted with ethyl acetate
  4. dry with materialthe combined organic phase is dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f382056666454a0a99a07bbe34dd4f15
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

Loading…