Succinic anhydride → HCID 67487353, compound

HRID 1755170Notes

Reaction equation

HRID 1755170 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-78bf3efe9c6a43dd97100ab10ddfa913
Source dataset
uspto-grants-2015_10
Patent number
US09169201B2

Reaction notes

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