Dimethylformamide → N-hydroxy-1-[4-methoxybenzenesulfonyl]-pyrrolidine-2(S)-carboxamide

HRID 2209675

反応式

HRID 2209675 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[C:17]([OH:19])=O)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.Cl.[NH2:32][OH:33].C(N(CC)CC)C>C(Cl)Cl.O1CCCC1.O>[OH:33][NH:32][C:17]([C@@H:13]1[CH2:14][CH2:15][CH2:16][N:12]1[S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])=[O:19]

参加物

9

反応物 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 7449021-[(4-Methoxyphenyl)sulfonyl]-D-proline

生成物 1

HCID 11022968N-hydroxy-1-[4-methoxybenzenesulfonyl]-pyrrolidine-2(S)-carboxamide

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

1-[4-Methoxybenzenesulfonyl]-pyrrolidine-2(R)-carboxylic acid (1.12 g, 3.93 mmol) is dissolved in methylene chloride (40.0 mL). To this solution is added oxalyl chloride (0.69 mL, 7.85 mmol) and dimethylformamide (0.30 mL, 3.93 mmol), and the reaction is stirred at room temperature for 30 minutes. Meanwhile, in a separate flask, hydroxylamine hydrochloride (1.1 g, 15.7 mmol) and triethylamine (3.3 mL, 23.5 mmol) are stirred in tetrahydrofuran (20.0 mL) and water (4.0 mL) at 0° C. for 15 minutes. After 30 minutes, the methylene chloride solution is added in one portion to the second flask, and the combined contents are stirred overnight as the flask gradually warms up to room temperature. The reaction is then diluted with acidic water (pH=~3), and extracted several times with ethyl acetate. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (50% ethyl acetate/hexane) to give N-hydroxy- 1-[4-methoxybenzenesulfonyl]-pyrrolidine-2(S)-carboxamide, m.p. 163.5°-165.5° C.

後処理

  1. waitAfter 30 minutes
  2. stirringthe combined contents are stirred overnight as the flask
  3. customgradually warms up to room temperature
  4. extractionextracted several times with ethyl acetate
  5. dry with materialThe combined organic layers are dried (MgSO4)
  6. customthe solvent is evaporated
  7. customThe product is purified by silica gel chromatography (50% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-54ea5ab8c1944453ae30d1892150db42
出典データセット
uspto-grants-1995_10
特許番号
US05455258

関連ノート

読み込み中…