Triethylamine → HCID 69359212, compound

HRID 852646Notes

Reaction equation

HRID 852646 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.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl.CN(C=O)C.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][S:26]([CH3:25])(=[O:28])=[O:27])[CH:5]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 674420033-Amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester

Product 1

HCID 69359212HCID 69359212, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (D4a) (200 mg, 0.85 mmol, 1 equiv) in CH2Cl2 (5 ml) and DMF (5 ml) was added NEt3 (0.181 ml, 1.3 mmol, 1.5 equiv) and methanesulphonyl chloride (0.071 ml, 1 mmol, 1.2 equiv). The resultant mixture was stirred at room temperature for 1 h, diluted with AcOEt (30 ml), washed with 2N aqueous HCl solution (30 ml), dried over MgSO4 and concentrated in vacuo. The residue was triturated with Et2O and then filtered to give 3-methanesulfonylamino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (B53) as a pale yellow solid (100 mg, 38%).

Workup

  1. washwashed with 2N aqueous HCl solution (30 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with Et2O
  5. filtrationfiltered

Sources & evidence

ORD record
ord-b98831e1743f4c60b8d073e918ce483a
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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