Water → HCID 15218405, compound

HRID 1611432Notes

Reaction equation

HRID 1611432 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-c75984835637490e85a50099605a8f8d
Source dataset
uspto-grants-2006_01
Patent number
US06987177B2

Reaction notes

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