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

HRID 852646노트

반응식

HRID 852646 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-b98831e1743f4c60b8d073e918ce483a
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253198B2

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