Succinic anhydride → HCID 67487353, compound

HRID 2371275Notes

Reaction equation

HRID 2371275 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:30][CH:29]=2)[C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2C2OC3=CC=CC3=CC=2)=[O:11])=[CH:4][CH:3]=1.[C:38]1(=[O:44])[O:43][C:41](=[O:42])[CH2:40][CH2:39]1.O1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1>C(OCC)C.C1(C)C=CC=CC=1>[O:48]1[C:49]2=[CH:50][CH:4]=[CH:3][C:2]2=[CH:7][CH:46]=[C:47]1[N:12]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:10]([CH:9]([C:28]1[CH:33]=[CH:32][C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:30][CH:29]=1)[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:41](=[O:42])[CH2:40][CH2:39][C:38]([OH:43])=[O:44])=[CH:7][CH:6]=1)=[O:11]

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 312751,4-DioxaneHCID 67486162HCID 67486162, compound

Product 1

HCID 67487353HCID 67487353, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
23 °C

Procedure

To 3-(4-Amino-phenyl)-N-(4-benzofuran-2-yl-phenyl)-2-(4-tert-butyl-phenyl)-propionamide (100 mg, 0.2 mmol) in 2 ml diethyl ether, 2 ml toluene and 1 ml 1,4-dioxane was added succinic anhydride (22 mg, 0.22 mmol). The reaction mixture was stirred at 23° C. for 16 h, concentrated, and loaded to reverse phase silica gel. After chromatography (from 20% acetonitrile to 80% acetonitrile in water in 12 column volume), the fractions containing the desired product were collected and concentrated. The residue was diluted with methanol (1 ml) and water was added dropwise until the precipitate stop forming. The white precipitate was removed by filtration and dried under high vacuum at 50° C. to afford the title compound (6.3 mg, 5%).

Workup

  1. concentrationconcentrated
  2. additionAfter chromatography (from 20% acetonitrile to 80% acetonitrile in water in 12 column volume), the fractions containing the desired product
  3. customwere collected
  4. concentrationconcentrated
  5. additionThe residue was diluted with methanol (1 ml) and water
  6. additionwas added dropwise until the precipitate stop
  7. customforming
  8. customThe white precipitate was removed by filtration
  9. customdried under high vacuum at 50° C.

Sources & evidence

ORD record
ord-6bdc15c309ef450aa250e4336b49356c
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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