Succinic anhydride → HCID 86666523, compound

HRID 1397107Notes

Reaction equation

HRID 1397107 reaction equation
[C:1]([O:12][CH2:13][CH:14]=[CH2:15])(=[O:11])[CH2:2][NH:3][CH2:4][C:5]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6].[C:16]1(=[O:22])[O:21][C:19](=[O:20])[CH2:18][CH2:17]1>C(Cl)(Cl)Cl>[CH2:13]([O:12][C:1]([CH2:2][N:3]([CH2:4][C:5]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6])[C:16]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[O:22])=[O:11])[CH:14]=[CH2:15]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 86666522HCID 86666522, compound

Product 1

HCID 86666523HCID 86666523, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Compound 9 (4.0 g, 10.39 mmol), succinic anhydride (1.04 g, 10.39 mmol), and 4-di(methylamino)pyridine (1.90 g, 15.59 mmol) were dissolved in CHCl3 (30 mL) and stirred for 24 h. The solvent was evaporated in vacuo and the crude material was purified by silica gel chromatography (40-80% EtOAc in hexanes) to give the compound 10 (1.66 g, 51%). 1H NMR (400 MHz, CDCl3) δ 2.64 (t, J=5.8, 2H), 2.70 (t, J=5.8, 2H), 4.21 (d, J=6.2, 4H), 4.61 (d, J=6.2, 2H), 4.65 (d, J=6.2, 2H), 5.22-5.35 (m, 4H), 5.89 (m, 2H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe crude material was purified by silica gel chromatography (40-80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-edc9f809e8984dbb92e7e8cd10b190be
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

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