Chlorosuccinimide → HCID 54477116, compound

HRID 398361Notes

Reaction equation

HRID 398361 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[CH:13]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:19]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:19][C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:11]=2)[NH:15][CH:14]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 29946181tert-Butyl [(1H-indol-5-yl)methyl]carbamate

Product 1

HCID 54477116HCID 54477116, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(t-butoxycarbonylaminomethyl)-indole (0.51 g, 2.05 mmol) in CH2Cl2, (12 mL) under Argon at 15°-20° C. was added N-chlorosuccinimide (0.245 g, 1.82 mmol) portionwise over 1 hr. The reaction stirred 0.5 h and was partitioned with H2O and CH2Cl2. The aquesous layer was extracted with CH2Cl2 (2×), dried over MgSO4, filtered, and concentrated in vacuo to a brown residue. Purification via flash chromatography (25×150 mm column; gradient elution with EtOAc: hexanes, 1:4 to 1:3) yielded a colorless oil:

Workup

  1. customwas partitioned with H2O and CH2Cl2
  2. extractionThe aquesous layer was extracted with CH2Cl2 (2×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a brown residue
  6. customPurification
  7. washvia flash chromatography (25×150 mm column; gradient elution with EtOAc: hexanes, 1:4 to 1:3)
  8. customyielded a colorless oil

Sources & evidence

ORD record
ord-e694038b36b14fd48d70c10424e8a06e
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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