Ammonium Hydroxide → HCID 86720294, compound

HRID 331057Notes

Reaction equation

HRID 331057 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8]2)(=[O:4])=[O:3].[OH-].[NH4+:22]>C1COCC1.O>[S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8]2)(=[O:4])(=[O:3])[NH2:22]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 867202951262408-03-6

Product 1

HCID 86720294HCID 86720294, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 5-(chlorosulfonyl)isoindoline-2-carboxylate (D97) (400 mg, 1.259 mmol) in THF (12 mL) was added ammonium hydroxide (0.490 mL, 12.59 mmol) at 0° C. The mixture was left to stir for 1 hour at RT. The mixture was concentrated in vacuo and the residue obtained taken up in water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organics were dried and concentrated down to afford the title compound (335 mg). LCMS (A): m/z (M−H)− 297, C13H18N2O4S requires 298 (acidic).

Workup

  1. waitThe mixture was left
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue obtained
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. customThe combined organics were dried
  6. concentrationconcentrated down

Sources & evidence

ORD record
ord-214547789ee64cd3a4eb6077e3e619f9
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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