Water → HCID 15218405, compound

HRID 1456844Notes

Reaction equation

HRID 1456844 reaction equation
[CH3:1][CH:2]([CH3:32])[C:3]([O:5][C@@H:6]1[C@@H:10]([CH2:11][O:12][C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])[O:9][C@@H:8]([N:18]2[C:22]3[N:23]=[C:24]([NH:29][CH:30]=[O:31])[N:25]=[C:26]([O:27][CH3:28])[C:21]=3[CH:20]=[CH:19]2)[CH2:7]1)=[O:4].[Br:33]N1C(=O)CCC1=O.C(Cl)Cl.O>CN(C)C=O.C([O-])(O)=O.[Na+]>[Br:33][C:20]1[C:21]2[C:26]([O:27][CH3:28])=[N:25][C:24]([NH:29][CH:30]=[O:31])=[N:23][C:22]=2[N:18]([C@@H:8]2[O:9][C@H:10]([CH2:11][O:12][C:13](=[O:17])[CH:14]([CH3:15])[CH3:16])[C@@H:6]([O:5][C:3](=[O:4])[CH:2]([CH3:32])[CH3:1])[CH2:7]2)[CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 11113110HCID 11113110, compound

Product 1

HCID 15218405HCID 15218405, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 516892Sodium BicarbonateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of compound 18 (10.1 mmol) in dimethylformamide was stirred, at room temperature for 1 hour, together with N-bromosuccinimide (10.1 mmol). A few drops of 5% aqueous NaHCO3 are added to the solution, in order to buffer it, and methylene chloride is then added. The organic phase is shaken with water, separated, dried over sodium sulfate and evaporated. Chromatography of the residue on a silica gel column in the eluent dichloromethane/acetone (95:5) results in two zones. The evaporation residue from the slowly migrating main zone yields colorless (19) (75%) as a solid.

Workup

  1. additionis then added
  2. customseparated
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customChromatography of the residue on a silica gel column in the eluent dichloromethane/acetone (95:5) results in two zones

Sources & evidence

ORD record
ord-675acce72d0f44778531a4c9fe57645f
Source dataset
uspto-grants-1998_12
Patent number
US05844106

Reaction notes

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