Triethylamine → Methyl 3-(methylsulfonamido)-5-(2-oxopyrrolidin-1-yl)benzoate

HRID 852646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852646
[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

Komponenten

7

Edukt 3

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

Produkt 1

HCID 69359212Methyl 3-(methylsulfonamido)-5-(2-oxopyrrolidin-1-yl)benzoateAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b98831e1743f4c60b8d073e918ce483a
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253198B2

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