Tetrahydrofuran → 2,5-dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate

HRID 593233Notes

Reaction equation

HRID 593233 reaction equation
[C:1]1(=[O:13])[N:6]([CH:7]([CH3:11])C(O)=O)[C:5](=[O:12])[CH2:4][CH:2]1O.[B-](F)(F)(F)F.CN([C:22]([O:26][N:27]1[C:32](=[O:33])[CH2:31][CH2:30][C:28]1=[O:29])=[N+](C)C)C.CCN(C(C)C)C(C)C.C1C[O:46]CC1>>[O:29]=[C:28]1[CH2:30][CH2:31][C:32](=[O:33])[N:27]1[O:26][C:22](=[O:46])[CH2:11][CH2:7][N:6]1[C:1](=[O:13])[CH:2]=[CH:4][C:5]1=[O:12]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 87524269HCID 87524269, compound

Product 1

HCID 46205972,5-dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate

Procedure

Malimidopropionic acid (500 mg) was dissolved in dry THF (15 ml). TSTU (790 mg) and DIPEA (0.62 ml) was added. The mixture was stirred at room temperature under nitrogen over night. The yellow thick suspension was concentrated. The residue was dissolved in DCM and extracted with 0.1 N HCl (2×) and brine (1×). The organic layer was dried (Na2SO4) and concentrated to give a white solid. LC-MS, M/z: 267.26 (M+1).

Workup

  1. concentrationThe yellow thick suspension was concentrated
  2. dissolutionThe residue was dissolved in DCM
  3. extractionextracted with 0.1 N HCl (2×) and brine (1×)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a white solid

Sources & evidence

ORD record
ord-32d28af8087048d59bce0516b2efff84
Source dataset
uspto-grants-2016_01
Patent number
US09242011B2

Reaction notes

Loading…