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Triethylamine → Toluene-4-thiosulfonic acid S-(2-tert-butyl-4-tert-butylsulfamoyloxy-5-methyl-phenyl) ester

HRID 356512
ノート
印刷プレビュー

反応式

HRID 356512 の反応式
[C:1]([C:5]1[CH:10]=[C:9]([OH:11])[C:8]([CH3:12])=[CH:7][C:6]=1[S:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[C:31]([NH:35][S:36](Cl)(=[O:38])=[O:37])([CH3:34])([CH3:33])[CH3:32]>CCOCC>[C:1]([C:5]1[CH:10]=[C:9]([O:11][S:36](=[O:38])(=[O:37])[NH:35][C:31]([CH3:34])([CH3:33])[CH3:32])[C:8]([CH3:12])=[CH:7][C:6]=1[S:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:15])=[O:16])([CH3:4])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471Triethylamine2 回HCID 10521842Toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxy-5-methyl-phenyl) esterHCID 12682606N-tert-butylsulfamoyl chloride2 回

生成物 1

HCID 54445851Toluene-4-thiosulfonic acid S-(2-tert-butyl-4-tert-butylsulfamoyloxy-5-methyl-phenyl) ester

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether
溶媒
3 回

反応条件

温度
0 °C

実験手順

To a round bottom flask equipped with a magnetic stirrer were added 1.10 g (3.20 mmol) of toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxy-5-methyl-phenyl) ester (prepared in Example RRR), Et2O (50 mL), and 0.90 mL (6.40 mmol) of NEt3, in that order. The solution was cooled to 0° C. To this solution was rapidly added a solution of 1.10 g (6.40 mmol) of (tert-butyl amino)sulfonyl chloride (Matler, W. L., Comer, W. T., and Deitchman, D., Journal of Medicinal Chemistry, 1972, 15 (5), 538-541) in Et2O (10 mL). A precipitate ensued and the reaction was allowed to stir for 30 minutes. Another two equivalents of (tert-butyl amino)sulfonyl chloride (1.10 g, 6.40 mmol) in Et2O (10 mL) and NEt3 (0.90 mL, 6.40 mmol) were added, and the reaction mixture was stirred for another 30 minutes. The reaction was quenched with brine and the organics extracted with Et2O. The organics were dried (MgSO4) and concentrated. The residue was submitted to flash chromatography (EtOAc:CHCl3 1:9) to yield the title compound. 1H NMR (CDCl3) δ 1.23 (s, 9 H), 1.46 (s, 9 H), 2.25 (s, 3 H), 2.42 (s, 3 H), 4.63 (br s, 1 H), 7.23 (s, 1 H), 7.26 (s, obscured by CDCl3, 1 H), 7.42 (d, 2 H), 7.46 (d, 2 H).

後処理

  1. customTo a round bottom flask equipped with a magnetic stirrer
  2. stirringthe reaction mixture was stirred for another 30 minutes
  3. customThe reaction was quenched with brine
  4. extractionthe organics extracted with Et2O
  5. dry with materialThe organics were dried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-c3f9826afbba43e2bb3baa327350639c
出典データセット
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05834506

反応ノート

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