Acetic Anhydride → HCID 11108632, compound

HRID 1181019Notes

Reaction equation

HRID 1181019 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH:5]([NH:9][C:10](=[O:19])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6]([OH:8])=O.[C:21](OC(=O)C)(=O)C>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH:5]([NH:9][C:10](=[O:19])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6](=[O:8])[CH3:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10989578HCID 10989578, compound

Product 1

HCID 11108632HCID 11108632, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

2-(3-Phenyl-propionylamino)-succinic acid 4-methyl ester (10 g, 36 mmol), pyridine (50 mL) and acetic anhydride (45 mL) were combined in a 500 mL flask. The reaction mixture was heated at 90° C. for 2 h and then cooled to ambient temperature. After concentrating the reaction mixture under reduced pressure, DI water was added (100 mL). The reaction mixture was partitioned between water and CH2Cl2 (200 mL). The organic phase was washed with 1N HCl (50 mL), dried (MgSO4), filtered, and concentrated. The material was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.31-7.20 (m, 5H), 6.79 (br d, J=7.6 Hz, 1H), 4.72 (X of ABX, 1H), 3.65 (s, 3H), 3.01-2.93 (m, 3H), 2.71-2.62 (m, 3H), 2.11 (s, 3H); MS (EI) 278.1 (M+H).

Workup

  1. temperaturecooled to ambient temperature
  2. concentrationAfter concentrating the reaction mixture under reduced pressure, DI water
  3. additionwas added (100 mL)
  4. customThe reaction mixture was partitioned between water and CH2Cl2 (200 mL)
  5. washThe organic phase was washed with 1N HCl (50 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe material was used without further purification

Sources & evidence

ORD record
ord-24962bd0b77a44abb36e23851cb56731
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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