Triethylamine → [(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-(3-dimethylamino-propoxy)-2,6-diisopropyl-phenyl ester

HRID 2289686ノート

反応式

HRID 2289686 の反応式
[H-].[Na+].[OH:3][C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[C:7]([O:13][S:14](=[O:35])(=[O:34])[NH:15][C:16](=[O:33])[CH2:17][C:18]2[C:23]([CH:24]([CH3:26])[CH3:25])=[CH:22][C:21]([CH:27]([CH3:29])[CH3:28])=[CH:20][C:19]=2[CH:30]([CH3:32])[CH3:31])=[C:6]([CH:36]([CH3:38])[CH3:37])[CH:5]=1.C(N(CC)CC)C.Cl.[CH3:47][N:48]([CH3:53])[CH2:49][CH2:50][CH2:51]Cl>CN(C)C=O.O1CCCC1.C(OCC)C>[CH3:47][N:48]([CH3:53])[CH2:49][CH2:50][CH2:51][O:3][C:4]1[CH:5]=[C:6]([CH:36]([CH3:38])[CH3:37])[C:7]([O:13][S:14](=[O:35])(=[O:34])[NH:15][C:16](=[O:33])[CH2:17][C:18]2[C:19]([CH:30]([CH3:32])[CH3:31])=[CH:20][C:21]([CH:27]([CH3:28])[CH3:29])=[CH:22][C:23]=2[CH:24]([CH3:25])[CH3:26])=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 24758Sodium hydrideHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 10142635[(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-hydroxy-2,6-diisopropyl-phenyl ester

生成物 1

HCID 10168301[(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-(3-dimethylamino-propoxy)-2,6-diisopropyl-phenyl ester収率 31.4%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Solid sodium hydride (0.16 g, 4 mmol) was added to a solution of [(2,4,6-triisopropyl-phenyl)-acetyl]-sulfamic acid 4-hydroxy-2,6-diisopropyl-phenyl ester (1.0 g, 1.9 mmol) in 50 mL of N,N-dimethylformamide. The resulting mixture was stirred for 1 hour before a mixture of triethylamine (1.08 mL, 7.8 mmol) and 3-dimethylaminopropylchloride hydrochloride (1.22 g, 3.9 mmol) in 75 mL tetrahydrofuran was added dropwise. The resulting mixture was stirred for 16 hours and then concentrated in vacuo. The residue was partitioned between saturated citric acid and dichloromethane. The organic layer was dried over magnesium sulfate, filtered, and concentrated to give an oily solid. Trituration with a small amount of diethyl ether gave 0.36 g of [(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-(3-dimethylamino-propoxy)-2,6-diisopropyl-phenyl ester as a white foam.

後処理

  1. additionwas added dropwise
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between saturated citric acid and dichloromethane
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oily solid

出典と根拠

ORDレコード
ord-ed8a7975289e44e49e187b0fb7b5a82c
出典データセット
uspto-grants-2000_07
特許番号
US06093744

反応ノート

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