Hydrochloric Acid → 1-Azabicyclo[3.2.2]non-5-yl(5-phenyl-1,3-thiazol-4-yl)carbamate

HRID 383957

反応式

HRID 383957 の反応式
[C:1]1([C:7]2[S:11][CH:10]=[N:9][C:8]=2C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC(P([N:29]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[N:32]12[CH2:40][CH2:39][C:36]([OH:41])([CH2:37][CH2:38]1)[CH2:35][CH2:34][CH2:33]2.Cl.[OH-].[Na+].CCO[C:48](C)=[O:49]>C1(C)C=CC=CC=1.CN(C=O)C>[N:32]12[CH2:40][CH2:39][C:36]([O:41][C:48](=[O:49])[NH:29][C:8]3[N:9]=[CH:10][S:11][C:7]=3[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([CH2:37][CH2:38]1)[CH2:35][CH2:34][CH2:33]2

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 8857Ethyl Acetate2 回HCID 14798Sodium HydroxideHCID 199401P,P-Diphenylphosphinic azideHCID 9448135-phenyl-1,3-thiazole-4-carboxylic AcidHCID 592915201-Azabicyclo[3.2.2]nonan-5-ol

生成物 1

HCID 248753771-Azabicyclo[3.2.2]non-5-yl(5-phenyl-1,3-thiazol-4-yl)carbamate

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-phenyl-1,3-thiazole-4-carboxylic acid (385 mg) in toluene (8 mL) was added TEA (285 μL) at room temperature. To the reaction mixture was added dropwise DPPA (404 μL), followed by stirring at the same temperature for 40 minutes. In addition, after stirring at 90° C. for 5 minutes, a mixture of 1-azabicyclo[3.2.2]nonan-5-ol (313 mg) and DMF (3 mL) was added thereto, followed by stirring at 110° C. for 1 hour. The reaction mixture was cooled to room temperature, followed by addition with 1 M hydrochloric acid for acidification, and extraction with EtOAc. The aqueous layer was alkalified with addition of a 1 M aqueous NaOH solution, and extracted with CHCl3. The organic layer was washed with water and brine in this order, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, CHCl3:MeOH:aqueous ammonia) to obtain a yellow amorphous fluorescent substance. To this was added EtOAc, and the resulting solid was collected by filtration, and washed with EtOAc to obtain 1-azabicyclo[3.2.2]non-5-yl(5-phenyl-1,3-thiazol-4-yl)carbamate (238 mg) as a colorless powder.

後処理

  1. stirringIn addition, after stirring at 90° C. for 5 minutes
  2. additionwas added
  3. stirringby stirring at 110° C. for 1 hour
  4. extractionextracted with CHCl3
  5. washThe organic layer was washed with water and brine in this order
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, CHCl3:MeOH:aqueous ammonia)
  9. customto obtain a yellow amorphous fluorescent substance
  10. filtrationthe resulting solid was collected by filtration
  11. washwashed with EtOAc

出典と根拠

ORDレコード
ord-36b441c5016649baacd06be6ab5d4ea5
出典データセット
uspto-grants-2013_02
特許番号
US08367696B2

関連ノート

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