Chlorosuccinimide → HCID 89037043, compound

HRID 331523Notes

Reaction equation

HRID 331523 reaction equation
[Cl:1]N1C(=O)CCC1=O.[OH:9]/[N:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:21][CH2:20][N:19]2[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[CH:14][CH:13]=1>CN(C)C=O.O>[Cl:1]/[C:11](/[C:12]1[CH:13]=[CH:14][C:15]([CH:18]2[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])[CH2:21][CH2:20][N:19]2[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[CH:16][CH:17]=1)=[N:10]\[OH:9]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 88996196HCID 88996196, compound

Product 1

HCID 89037043HCID 89037043, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

N-chlorosuccinimide (239.0 mg, 1.790 mmol) was added to a stirred suspension of (E)-di-tert-butyl 2-(4-((hydroxyimino)methyl)phenyl)piperazine-1,4-dicarboxylate (725.8 mg, 1.790 mmol) in N,N-dimethyl formamide (10 mL). The reaction was then heated at 55° C. for 1 hour. The reaction was cooled to ambient temperature and diluted with water. The reaction mixture was extracted with ethyl acetate (×3). Organic extracts were combined, dried over MgSO4, filtered and concentrated in vacuo. The sub-titled compound was used directly in the next step without further purification. (787.5 mg, assume 100% yield).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. extractionThe reaction mixture was extracted with ethyl acetate (×3)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe sub-titled compound was used directly in the next step without further purification

Sources & evidence

ORD record
ord-19e1e8e3941646e7a7951135a6b50f44
Source dataset
uspto-grants-2014_11
Patent number
US08877759B2

Reaction notes

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