Chlorosuccinimide → HCID 57774200, compound

HRID 656366Notes

Reaction equation

HRID 656366 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@:6]1([C:14](=[O:15])[NH:13][C:12](=[O:16])[N:11]1[CH3:17])[CH2:5]2.[Cl:18]N1C(=O)CCC1=O>CC(O)=O>[NH2:1][C:2]1[C:3]([Cl:18])=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@:6]1([C:14](=[O:15])[NH:13][C:12](=[O:16])[N:11]1[CH3:17])[CH2:5]2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 57774196HCID 57774196, compound2×

Product 1

HCID 57774200HCID 57774200, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(R)-5′-Amino-3-methyl-spiro[imidazolidine-4,2′-indane]-2,5-dione (265 mg, 1.15 mmol, described in Intermediate 8) was dissolved in AcOH (7 mL) and N-chlorosuccinimide (145 mg, 1.09 mmol) was added in one portion. The mixture was stirred at ambient temperature for 5 h, then the solvent was removed in vacuo. The residue was partitioned between saturated aqueous NaHCO3 (20 mL) and CH2Cl2 (70 mL). The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc—100:0 to 0:100, to give (R)-5′-amino-4′-chloro-3-methyl-spiro[imidazolidine-4,2′-indane]-2,5-dione, which eluted first, and the title compound, which eluted second. MS: m/z=266 (M+1).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between saturated aqueous NaHCO3 (20 mL) and CH2Cl2 (70 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-90a7e65170254e95a58e642ecdf63a81
Source dataset
uspto-grants-2011_12
Patent number
US08071770B2

Reaction notes

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