Benzyl succinimido carbonate → HCID 57842737, compound

HRID 735567Notes

Reaction equation

HRID 735567 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[NH2:6].[C:15](=O)([O:24]N1C(=O)CCC1=O)[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.C(Cl)Cl>[NH2:6][C:5]1[CH:7]=[CH:8][C:9]([S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])=[C:3]([CH:4]=1)[CH2:2][NH:1][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 684177793-(Aminomethyl)-4-(ethylsulfonyl)aniline

Product 1

HCID 57842737HCID 57842737, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(aminomethyl)-4-(ethylsulfonyl)aniline (1.1 g, 5.1 mmol) in DMF (5 mL) and TEA (2.75 mL) was added benzyl 2,5-dioxopyrrolidin-1-yl carbonate (1.4 g, 5.7 mmol) in DCM (15 mL). The solution was stirred for 18 h before quenching with water (25 mL). The reaction mixture was extracted with DCM (2×30 mL), washed with brine and dried (MgSO4). The organic layer was concentrated in vacuo and the residue purified by flash chromatography (0-100% EtOAc/Hexane) to afford 28A (1.0 g, 59%) as an oil. MS (ESI) m/z 349.2 (M+H)+.

Workup

  1. custombefore quenching with water (25 mL)
  2. extractionThe reaction mixture was extracted with DCM (2×30 mL)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe residue purified by flash chromatography (0-100% EtOAc/Hexane)

Sources & evidence

ORD record
ord-453336f213d6455388e7a5de3ec49729
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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