Benzoyl chloride, 3-chloro- → HCID 68303804, compound

HRID 1846625Notes

Reaction equation

HRID 1846625 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:17]([NH2:18])=[CH:16][C:15]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][N:13]=2)[CH2:8][CH2:7]1)[CH3:2].[Cl:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=[O:29]>C(#N)C>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:17]([NH:18][C:28](=[O:29])[C:27]3[CH:31]=[CH:32][CH:33]=[C:25]([Cl:24])[CH:26]=3)=[CH:16][C:15]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][N:13]=2)[CH2:8][CH2:7]1)[CH3:2]

Participants

4

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 67341530HCID 67341530, compound

Product 1

HCID 68303804HCID 68303804, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1.65 g (4.83 mmol) of (3′-amino-5′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid ethyl ester in acetonitrile (100 mL) is added 0.64 mL (5.0 mmol) of 3-chlorobenzoyl chloride. After stirring at room temperature overnight the mixture is concentrated under reduced pressure. The residue is diluted with water and extracted with ethyl acetate. The combined organic phase is dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by flash silica gel chromatography to provide 1.40 g (60.4%) of [3′-(3-chloro-benzoylamino)-5′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid ethyl ester as a white foam.

Workup

  1. concentrationis concentrated under reduced pressure
  2. additionThe residue is diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phase is dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by flash silica gel chromatography

Sources & evidence

ORD record
ord-eccfeb722bce466cb01bcc1229a4b3fa
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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