Acetonitrile → HCID 11032835, compound

HRID 595965Notes

Reaction equation

HRID 595965 reaction equation
[NH2:1][C@@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].C(#N)C.[C:14](ON1C(=O)CCC1=O)(=[O:25])[C:15]1[C:16](=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:17](OC)=[O:18]>O>[OH:4][CH2:3][C@@H:2]([N:1]1[C:17](=[O:18])[C:16]2[C:15](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]1=[O:25])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 1347972-Amino-2-phenylethan-1-olHCID 10901878Methyl 2-[(succinimidooxy)carbonyl]benzoate

Product 1

HCID 11032835HCID 11032835, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (S)-2-amino-2-phenylethanol (3 g, 21.87 mmol) in water (26.5 mL), and acetonitrile (46.4 mL) was added 2,5-dioxopyrrolidin-1-yl methyl phthalate (5.76 g, 20.78 mmol) at room temperature. The reaction mixture was stirred at room temperature for overnight. After acetonitrile was removed in vacuo, the reaction mixture was then extracted with EtOAc. The organic was washed by water and brine, dried over anhydrous sodium sulfate, filtered off, and concentrated in vacuo yielding (S)-2-(2-hydroxy-1-phenylethyl)isoindoline-1,3-dione (2.2 g, 40%). LCMS (m/z): 268 (MH+), 0.79 min.

Workup

  1. customAfter acetonitrile was removed in vacuo
  2. extractionthe reaction mixture was then extracted with EtOAc
  3. washThe organic was washed by water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered off
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eed24d4ce7e446cc9b2ad05dc5cb950b
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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