Acetic Anhydride → HCID 68771702, compound

HRID 2265194Notes

Reaction equation

HRID 2265194 reaction equation
[C:1]1([C@H:7]([CH3:17])[CH2:8][NH:9][C:10](/[CH:12]=[CH:13]/[C:14]([OH:16])=O)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC([O-])=O.[Na+].CC(OC(C)=O)=O>>[C:1]1([C@H:7]([CH3:17])[CH2:8][N:9]2[C:10](=[O:11])[CH:12]=[CH:13][C:14]2=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 68768578HCID 68768578, compound

Product 1

HCID 68771702HCID 68771702, compoundYield 26%

Conditions

Temperature
120 °C

Procedure

A mixture of (S)-E-3-(2-phenyl-propylcarbamoyl)-acrylic acid (1.44 g, 6.2 mmol), NaOAc (305 mg, 3.7 mmol), and Ac2O (6 mL) was heated at 120° C. for 5 h. The mixture was concentrated, and the residue was stirred vigorously with satd. aq. NaHCO3. The resulting mixture was extracted with DCM (3×). The combined organic layers were dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (EtOAc/hexanes) to provide 340 mg (26%) of the desired maleimide as a white solid. 1H NMR (400 MHz, CDCl3): 7.32-7.26 (m, 2H), 7.24-7.17 (m, 3H), 6.60 (s, 2H), 3.70 (dd, J=13.7, 8.2, 1H), 3.61 (dd, J=13.7, 7.8, 1H), 3.23 (app. sextet, J=7.7, 1H), 1.26 (d, J=7.0, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionThe resulting mixture was extracted with DCM (3×)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-84c9f6bb84524f0eb9f3f45bfcb860ae
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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