Acetic Anhydride → HCID 22253013, compound

HRID 852645Notes

Reaction equation

HRID 852645 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([NH2:16])[CH:5]=1.CCN(CC)CC.[C:25](OC(=O)C)(=[O:27])[CH3:26]>C(Cl)Cl.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([NH:16][C:25](=[O:27])[CH3:26])[CH:5]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 674420033-Amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester

Product 1

HCID 22253013HCID 22253013, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (D4a) (80 mg, 0.34 mmol, 1 equiv) in CH2Cl2 (10 ml) was added NEt3 (0.142 ml, 1.02 mmol, 2 equiv) and acetic anhydride (0.078 ml, 0.82 mmol, 2.4 equiv). The resulting mixture was stirred at room temperature for 16 h. The reaction was then diluted with AcOEt (20 ml), washed with 2N aqueous HCl solution (20 ml), dried over MgSO4, and concentrated in vacuo to give 3-acetylamino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (B50) (67 mg, 71%) as a pale yellow foam.

Workup

  1. washwashed with 2N aqueous HCl solution (20 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5dba07018964d7a95edec41bea52829
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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