Pyridine → HCID 20078937, compound

HRID 1653963Notes

Reaction equation

HRID 1653963 reaction equation
[Cl:1][C:2]1[C:7]([S:8][CH2:9][C:10]([O:12][CH:13]2[CH:17]([OH:18])[CH2:16][O:15][CH2:14]2)=[O:11])=[CH:6][C:5]([N:19]=[C:20]2[N:28]3[N:23]([CH2:24][CH2:25][CH2:26][CH2:27]3)[C:22](=[O:29])[S:21]2)=[C:4]([F:30])[CH:3]=1.N1C=CC=CC=1.[Cl:37][CH2:38][C:39](Cl)=[O:40]>ClCCl>[Cl:1][C:2]1[C:7]([S:8][CH2:9][C:10]([O:12][CH:13]2[CH:17]([O:18][C:39](=[O:40])[CH2:38][Cl:37])[CH2:16][O:15][CH2:14]2)=[O:11])=[CH:6][C:5]([N:19]=[C:20]2[N:28]3[N:23]([CH2:24][CH2:25][CH2:26][CH2:27]3)[C:22](=[O:29])[S:21]2)=[C:4]([F:30])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 15789802HCID 15789802, compound

Product 1

HCID 20078937HCID 20078937, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 25 ml of dichloromethane were dissolved 1.19 g of 9-(4-chloro-2-fluoro-5-(4-hydroxytetrahydrofuran-3-yloxycarbonylmethylthio)phenylimino)- 8-thia-1,6diazabicyclo[4.3.0]nonan-7-one and 0.24 g of pyridine, followed by dropwise addition of a solution of 0.34 g of chloroacetyl chloride in dichloromethane. After stirring at room temperature overnight, the reaction mixture was washed with water, and subsequently with aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by chromatography on a silica gel column (eluted with ethyl acetate/hexane =2/3), to obtain 1.02 g of a compound described in Table 1 (No. 32) (74%).

Workup

  1. washthe reaction mixture was washed with water
  2. dry with materialsubsequently with aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  3. distillationAfter distilling off the solvent
  4. customthe residue was purified by chromatography on a silica gel column (eluted with ethyl acetate/hexane =2/3)

Sources & evidence

ORD record
ord-d5609dab824142dc80f6ddc709232214
Source dataset
uspto-grants-1995_04
Patent number
US05405828

Reaction notes

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