Water → Hexaethyldisiloxane

HRID 890615ノート

反応式

HRID 890615 の反応式
CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@@H](C/C=C/C)C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](C[CH:81]([CH3:83])C)N(C)C(=O)CN(C)C1=O.FC(F)(F)S([O:91][Si:92]([CH2:97][CH3:98])([CH2:95][CH3:96])[CH2:93][CH3:94])(=O)=O.O>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH2:93]([Si:92]([O:91][Si:92]([CH2:81][CH3:83])([CH2:95][CH3:96])[CH2:93][CH3:94])([CH2:97][CH3:98])[CH2:95][CH3:96])[CH3:94]

参加物

6

反応物 3

HCID 962WaterHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 5284373Cyclosporin A

生成物 1

HCID 70442Hexaethyldisiloxane

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

Cyclosporin A (3.606 g, 3 mmol) was dissolved in dry pyridine (8 mL) and then DMAP (122 mg, 1 mmol) was added. The reaction mixture was cooled to 0° C. and then triethylsilyl trifluoromethanesulfonate (3.6 mmol) added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was then poured slowly into water with stirring. The precipitated triethylsilyl ether was filtered off and washed with water. The collected cake was dissolved in a minimum volume of methanol and added to a 5% citric acid solution and stirred for 30 minutes. The precipitated product was collected by filtration and washed with water until the pH of the filtrate reached that of the water. The solid triethylsilyl ether was dried at 50° C. under vacuum to give a colorless solid. Triisopropylsilyl and tert-butyldimethylsilyl protecting groups were also introduced by following an analogous procedure.

後処理

  1. temperatureto warm to room temperature
  2. stirringwith stirring
  3. filtrationThe precipitated triethylsilyl ether was filtered off
  4. washwashed with water
  5. dissolutionThe collected cake was dissolved in a minimum volume of methanol
  6. additionadded to a 5% citric acid solution
  7. stirringstirred for 30 minutes
  8. filtrationThe precipitated product was collected by filtration
  9. washwashed with water until the pH of the filtrate
  10. dry with materialThe solid triethylsilyl ether was dried at 50° C. under vacuum
  11. customto give a colorless solid
  12. additionTriisopropylsilyl and tert-butyldimethylsilyl protecting groups were also introduced

出典と根拠

ORDレコード
ord-0e5eb25b6d804d4ba1b90f7cfaaa05f8
出典データセット
uspto-grants-2006_02
特許番号
US06998385B2

反応ノート

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