Propofol → Dodecyl[[2,6-Bis(1-methylethyl)phenoxy]sulfonyl]carbamate

HRID 5642

反応式

HRID 5642 の反応式
[CH2:1]([O:13][C:14](=[O:20])[NH:15][S:16](Cl)(=[O:18])=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[C:25]=1[OH:33])([CH3:23])[CH3:22].C(N(CC)CC)C>C1COCC1>[CH3:31][CH:30]([C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([CH:21]([CH3:23])[CH3:22])[C:25]=1[O:33][S:16]([NH:15][C:14](=[O:20])[O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:17])=[O:18])[CH3:32]

参加物

5

反応物 3

HCID 4943PropofolHCID 8471TriethylamineHCID 10758631Dodecyl(chlorosulfonyl)carbamate

生成物 1

HCID 10648021Dodecyl[[2,6-Bis(1-methylethyl)phenoxy]sulfonyl]carbamate収率 59.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of n-dodecyl(chlorosulfonyl)carbamate (5.0 g, 15.2 mmoles) in 80 mL THF was added dropwise to a solution of 2,6-diisopropyl phenol (2.72 g, 15.2 mmoles) and excess triethylamine in 100 mL THF at room temperature under an atmosphere of N2. The mixture was stirred for 16 hours and then concentrated in vacuo. The residue was partitioned between 1N HCl and EtOAc. The organic layer was dried with MgSO4, filtered, and evaporated to give a clear oil. Chromatography (SiO2, 5% EtOAc/hexanes) gave 4.26 g of the title compound as a waxy solid, mp 32°-35° C.

後処理

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between 1N HCl and EtOAc
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give a clear oil

出典と根拠

ORDレコード
ord-29c831e9f5614f9b8eb8037523a00d0e
出典データセット
uspto-grants-1993_09
特許番号
US05245068

関連ノート

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