Acetic Anhydride → HCID 20823162, compound

HRID 1393472Notes

Reaction equation

HRID 1393472 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH:5]([NH:9][C:10]([C:12]1[S:13][C:14]([CH3:17])=[CH:15][CH:16]=1)=[O:11])[C:6]([OH:8])=O.[C:19](OC(=O)C)(=O)C>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH:5]([NH:9][C:10]([C:12]1[S:13][C:14]([CH3:17])=[CH:15][CH:16]=1)=[O:11])[C:6](=[O:8])[CH3:19]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 20823125HCID 20823125, compound

Product 1

HCID 20823162HCID 20823162, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

2-[(5-Methyl-thiophene-2-carbonyl)-amino]-succinic acid 4-methyl ester (12 g, 45 mmol), pyridine (60 mL) and acetic anhydride (50 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). (Potential exotherm!). The reaction mixture was partitioned between water and CH2Cl2. The organic phase was washed with 1N HCl and then dried (MgSO4), filtered and concentrated under reduced pressure. The material was used without further purification. MS (EI) 270.1 (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
  5. washThe organic phase was washed with 1N HCl
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe material was used without further purification

Sources & evidence

ORD record
ord-85da7f2a3d42482f8860cf05cabc48f6
Source dataset
uspto-grants-2008_03
Patent number
US07345070B2

Reaction notes

Loading…