Triethylamine → 4-[2-(1,1-Dioxo-isothiazolidin-2-yl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1728112ノート

反応式

HRID 1728112 の反応式
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][NH2:16])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.Cl[CH2:25][CH2:26][CH2:27][S:28](Cl)(=[O:30])=[O:29]>C1COCC1>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][N:16]2[CH2:25][CH2:26][CH2:27][S:28]2(=[O:30])=[O:29])[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 1514400tert-Butyl 4-(2-aminoethyl)piperazine-1-carboxylate

生成物 1

HCID 575660704-[2-(1,1-Dioxo-isothiazolidin-2-yl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 1-Boc-4-(2-aminoethyl)-piperazine (1.26 g, 6.8 mmol) and triethylamine (1 mL) in THF (10 ML), 3-chloro-propylsulfonyl chloride (Aldrich, 0.68 mL, 6.94 mmol) was added slowly at room temperature. The mixture was stirred for 30 minutes at and the reaction was quenched with water. The new mixture was extracted with ethyl acetate and the extracts were combined and dried (Na2SO4). The solution was concentrated and the residue was dissolved in THF (20 mL) and Cs2CO3 (500 mg), NaI (80 mg) were added and the mixture was stirred at reflux overnight. The mixture was cooled to room temperature and poured into water. The new mixture was extracted with ethyl acetate (3×15 mL) and the extracts were combined and dried (Na2SO4). Removal of the solvent on a rotary evaporator gave a solid. 2.01 g.

後処理

  1. customwas quenched with water
  2. extractionThe new mixture was extracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. concentrationThe solution was concentrated
  5. dissolutionthe residue was dissolved in THF (20 mL)
  6. additionCs2CO3 (500 mg), NaI (80 mg) were added
  7. stirringthe mixture was stirred
  8. temperatureat reflux overnight
  9. additionpoured into water
  10. extractionThe new mixture was extracted with ethyl acetate (3×15 mL)
  11. dry with materialdried (Na2SO4)
  12. customRemoval of the solvent
  13. customon a rotary evaporator
  14. customgave a solid

出典と根拠

ORDレコード
ord-1022d81cd44f481baa69582f04df677c
出典データセット
uspto-grants-2009_02
特許番号
US07495007B2

反応ノート

読み込み中…