4-Methylmorpholine → trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxamide

HRID 5396

反応式

HRID 5396 の反応式
[C:1]([S:4][CH2:5][C@H:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:16](O)=[O:17])[NH:8][C:7]1=[O:19])(=[O:3])[CH3:2].C[N:21]1CCOCC1.ClC(OCC)=O>O1CCCC1.C(Cl)Cl>[C:1]([S:4][CH2:5][C@H:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:16]([NH2:21])=[O:17])[NH:8][C:7]1=[O:19])(=[O:3])[CH3:2]

参加物

6

反応物 3

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 86747202trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid

生成物 1

HCID 86747204trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid (0.30 g, 1.05 mmol) is dissolved in tetrahydrofuran (5.0 mL). 4-Methylmorpholine (0.14 mL, 1.05 mmol) is then added, and the reaction is cooled to -20° C. Ethyl chloroformate (0.1 mL, 1.05 mmol) is then added, and the reaction is stirred at -20° C. for 30 minutes. The reaction is then filtered, and the filtrate is concentrated to give a yellow oil. This oil is dissolved in methylene chloride (20.0 mL), and anhydrous ammonia gas is bubbled through the solution for 1 hour. The bubbling is stopped, and the reaction is stirred an additional 1 hour. The solvent is evaporated, and the residue is partitioned between ethyl acetate and water. The aqueous layer is extracted several times with ethyl acetate, the combined organic layers are dried (Na2SO4), and the solvent is evaporated to give trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxamide, MS:M+1=287.

後処理

  1. filtrationThe reaction is then filtered
  2. concentrationthe filtrate is concentrated
  3. customto give a yellow oil
  4. customanhydrous ammonia gas is bubbled through the solution for 1 hour
  5. stirringthe reaction is stirred an additional 1 hour
  6. customThe solvent is evaporated
  7. customthe residue is partitioned between ethyl acetate and water
  8. extractionThe aqueous layer is extracted several times with ethyl acetate
  9. dry with materialthe combined organic layers are dried (Na2SO4)
  10. customthe solvent is evaporated

出典と根拠

ORDレコード
ord-6d7f78a9e4854515844933e38954e2d1
出典データセット
uspto-grants-1993_09
特許番号
US05244889

関連ノート

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