Sodium hydride → HCID 86755435、化合物

HRID 1420582ノート

反応式

HRID 1420582 の反応式
[C:1]([O:5][C:6](=[O:22])[CH:7]([NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH2:8][OH:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[N+:25]([C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH2:30]Br)([O-:27])=[O:26]>CN(C)C=O>[OH:9][CH2:8][CH:7]([N:10]([S:11]([C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)(=[O:13])=[O:12])[CH2:30][C:29]1[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=1[N+:25]([O-:27])=[O:26])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:22]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 77569alpha-Bromo-2-nitrotoluene2 回HCID 539780843-Hydroxy-2-(4-methoxybenzenesulfonylamino)-propionic acid tert-butyl ester

生成物 1

HCID 86755435HCID 86755435、化合物収率 129.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To 6.16 g (18.6 mmol) of 3-hydroxy-2-(4-methoxybenzenesulfonylamino)-propionic acid tert-butyl ester in 50 ml of N,N-dimethylformamide, cooled in an ice bath, was added 0.781 g (19.5 mmol) of sodium hydride. After gas evolution ceased, a solution of 4.02 g (18.6 mmol) of 2-nitrobenzylbromide in 18 ml of N,N-dimethylformamide was added dropwise. The mixture was stirred under nitrogen at room temperature for 4 hours and 1.0 g of 2-nitrobenzyl bromide was added. The mixture was stirred at room temperature overnight and the solvent removed under vacuum. The residue was diluted with water and extracted with CH2Cl2. The organic extract was washed with H2O, brine and dried with Na2SO4. The solvent was removed to give 11.2 g of solid which was chromatographed on silica gel with hexane-ethyl acetate (1:1) as eluent followed by hexane-ethyl acetate (35:65) as eluent. The fractions containing product were combined and the solvent was then removed to gave 7.7 g (89%) of solid. A sample from a 3 mmol run gave a gum. Anal. for C21H26N2O8S: Calc'd: C,54.1; H,5.6; N,6.0; Found: C,54.0; H,5.7; N,6.0.

後処理

  1. stirringThe mixture was stirred at room temperature overnight
  2. customthe solvent removed under vacuum
  3. additionThe residue was diluted with water
  4. extractionextracted with CH2Cl2
  5. extractionThe organic extract
  6. washwas washed with H2O, brine
  7. dry with materialdried with Na2SO4
  8. customThe solvent was removed

出典と根拠

ORDレコード
ord-23beff8fff8c49b494e3b0890211d6ab
出典データセット
uspto-grants-2000_06
特許番号
US06071903

反応ノート

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