Triethylamine → HCID 59408251、化合物

HRID 1515353ノート

反応式

HRID 1515353 の反応式
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[O:20]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[NH:23][CH2:22][CH2:21]1.[NH2:30][CH:31]1[CH:38]2[CH2:39][C:34]3([C:41]([O:43][CH3:44])=[O:42])[CH2:35][CH:36]([CH2:40][CH:32]1[CH2:33]3)[CH2:37]2>C(Cl)(Cl)Cl.C(OCC)(=O)C>[O:20]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]([C:2]([NH:30][CH:31]2[CH:38]3[CH2:39][C:34]4([C:41]([O:43][CH3:44])=[O:42])[CH2:35][CH:36]([CH2:40][CH:32]2[CH2:33]4)[CH2:37]3)=[O:4])[CH2:22][CH2:21]1

参加物

7

反応物 4

HCID 8471Triethylamine2 回HCID 94429TriphosgeneHCID 5850963,4-Dihydro-2H-1,4-benzoxazineHCID 57425932Methyl 4-aminoadamantane-1-carboxylate

生成物 1

HCID 59408251HCID 59408251、化合物

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of triphosgene (223 mg) in chloroform (5 ml), a solution of triethylamine (0.31 ml) and 3,4-dihydro-2H-1,4-benzoxazine obtained in Reference Example 14 (203 mg) in chloroform (2 ml) was added under ice cooling and stirred at the same temperature for 10 minutes. To the reaction mixture, methyl 4-aminoadamantane-1-carboxylate obtained in Reference Example 11 (314 mg) and triethylamine (0.31 ml) were then added and stirred under ice cooling for 3 hours. The reaction mixture was warmed to room temperature and further stirred for 16 hours. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed sequentially with water, 1M aqueous hydrochloric acid, saturated aqueous sodium bicarbonate and brine. After drying over anhydrous magnesium sulfate, the desiccant was filtered off and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=4:1 to 1:1) to give an isomer mixture of the titled compounds (a mixture of Compounds 35a and 35b, 474 mg) as a light-yellow amorphous substance.

後処理

  1. additionwas added under ice cooling
  2. additionwere then added
  3. stirringstirred under ice cooling for 3 hours
  4. stirringfurther stirred for 16 hours
  5. washthe organic layer was washed sequentially with water, 1M aqueous hydrochloric acid, saturated aqueous sodium bicarbonate and brine
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. filtrationthe desiccant was filtered off
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=4:1 to 1:1)
  10. customto give

出典と根拠

ORDレコード
ord-29800e33690f45209b4554eb6559d4cc
出典データセット
uspto-grants-2012_07
特許番号
US08222417B2

反応ノート

読み込み中…