Water → tert-butyl N-(3-{[(tert-butoxycarbonyl)sulfamoyl]amino}benzyl)-N-(trifluoroacetyl)glycinate

HRID 1497514ノート

反応式

HRID 1497514 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][N:6]([C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C(N(CC)CC)C.Cl[S:32]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])(=[O:34])=[O:33].O>ClCCl>[C:38]([O:37][C:36]([NH:35][S:32]([NH:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][N:6]([C:15](=[O:20])[C:16]([F:17])([F:18])[F:19])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])(=[O:34])=[O:33])=[O:42])([CH3:41])([CH3:39])[CH3:40]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 15677406tert-butyl N-(chlorosulfonyl)carbamateHCID 90282000tert-butyl N-(3-aminobenzyl)-N-(trifluoroacetyl)glycinate

生成物 1

HCID 90282078tert-butyl N-(3-{[(tert-butoxycarbonyl)sulfamoyl]amino}benzyl)-N-(trifluoroacetyl)glycinate収率 73%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of tert-butyl N-(3-aminobenzyl)-N-(trifluoroacetyl)glycinate (1.95 g) and triethylamine (0.981 mL) in dichloromethane (19.5 mL) was added a solution of tert-butyl (chlorosulfonyl)carbamate (1.52 g) in dichloromethane (10.0 mL) under ice-cooling, followed by stirring at room temperature for 3 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue was added ethyl acetate, and n-hexane was added thereto. The precipitated solid was collected by filtration to obtain tert-butyl N-(3-{[(tert-butoxycarbonyl)sulfamoyl]amino}benzyl)-N-(trifluoroacetyl)glycinate (2.19 g).

後処理

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materiala saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue was added ethyl acetate, and n-hexane
  7. additionwas added
  8. filtrationThe precipitated solid was collected by filtration

出典と根拠

ORDレコード
ord-ab444a29f427438982f56848eaefccda
出典データセット
uspto-grants-2015_12
特許番号
US09199927B2

反応ノート

読み込み中…