8-Aminooctanoic acid → HCID 66968126, compound

HRID 593234Notes

Reaction equation

HRID 593234 reaction equation
O=C1CCC(=O)N1O[C:9](=[O:19])[CH2:10][CH2:11][N:12]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]1=[O:18].[NH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29].CCN(C(C)C)C(C)C>CN(C=O)C>[O:17]=[C:16]1[CH:15]=[CH:14][C:13](=[O:18])[N:12]1[CH2:11][CH2:10][C:9]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:19]

Participants

5

Reactant 3

HCID 660858-Aminooctanoic acidHCID 81531DiisopropylethylamineHCID 46205972,5-dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate

Product 1

HCID 66968126HCID 66968126, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(2,5-Dioxo-2,5-dihydropyrrol-1-yl)propionic acid 2,5-dioxopyrrolidin-1-yl ester (787 mg, crude) was dissolved in DMF (15 ml). 8-Aminooctanoic acid (350 mg) and DIPEA (0.45 ml) was added. The mixture was stirred under nitrogen at room temperature over night. The mixture was concentrated. The residue was dissolved in EtOAc and extracted with 0.1 N HCl (2×). The phase separation was not easy. The organic layer was washed with brine (2×), dried (Na2SO4) and concentrated to give a white solid. LC-MS, M/z: 311.34 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. extractionextracted with 0.1 N HCl (2×)
  4. customThe phase separation
  5. washThe organic layer was washed with brine (2×)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customto give a white solid

Sources & evidence

ORD record
ord-7f967e2f4d284b8b9a8b8deb493eacb2
Source dataset
uspto-grants-2016_01
Patent number
US09242011B2

Reaction notes

Loading…