Acetic Acid → 3-Azido-5-phenyl-1-(2,2,2-trifluoroethyl)-1H-benzo[e][1,4]diazepine-2-one

HRID 1458968ノート

反応式

HRID 1458968 の反応式
[C:1]1([C:7]2[C:8]3[CH:23]=[CH:22][CH:21]=[CH:20][C:9]=3[N:10]([CH2:15][C:16]([F:19])([F:18])[F:17])[C:11](=[O:14])[CH2:12][N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].C(C1C=C(C(C)C)C=C(C(C)C)C=1S([N:48]=[N+:49]=[N-:50])(=O)=O)(C)C.C(O)(=O)C.C([O-])(O)=O.[Na+]>C1COCC1>[N:48]([CH:12]1[C:11](=[O:14])[N:10]([CH2:15][C:16]([F:18])([F:19])[F:17])[C:9]2[CH:20]=[CH:21][CH:22]=[CH:23][C:8]=2[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:13]1)=[N+:49]=[N-:50]

参加物

7

反応物 5

HCID 176Acetic AcidHCID 3717072,4,6-Triisopropylbenzenesulfonyl azideHCID 516892Sodium BicarbonateHCID 111416741-(2,2,2-Trifluoroethyl)-5-phenyl-1H-1,4-benzodiazepine-2(3H)-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 189689903-Azido-5-phenyl-1-(2,2,2-trifluoroethyl)-1H-benzo[e][1,4]diazepine-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a stirring solution of 5-phenyl-1-(2,2,2-trifluoroethyl)-1H-benzo[e][1,4]diazepine-2-one (66 g,0.209 mole) in THF (1200 mL) cooled to -78° C. was added potassium tert-butoxide (229 mL of a 1N solution in THF dropwise over 30 min. A solution of the anion was obtained. A solution of 2,4,6-triisopropylbenzenesulfonylazide (71 g, 0.229 mole) in THF (200 mL) was added over 20 min. This was stirred for 10 min, acetic acid (50 g, 48 ml, 0.834 mole) was added and the reaction allowed to warm to ambient temperature over 4 hours. The reaction was poured into sat. NaHCO3 (1 L) and extracted with ethyl acetate (2×500 mL). The organic layers were combined, washed once with water then brine, dried with Na2 SO4 and evaporated at reduced pressure. The residue was dissolved in THF (500 mL) and then filtered to give a solid which was discarded. The solution of crude azide was used without further purification.

後処理

  1. customA solution of the anion was obtained
  2. extractionextracted with ethyl acetate (2×500 mL)
  3. washwashed once with water
  4. dry with materialbrine, dried with Na2 SO4
  5. customevaporated at reduced pressure
  6. dissolutionThe residue was dissolved in THF (500 mL)
  7. filtrationfiltered
  8. customto give a solid which
  9. customThe solution of crude azide was used without further purification

出典と根拠

ORDレコード
ord-59e13a60f42d4e86a51ef96b6c96f965
出典データセット
uspto-grants-1998_12
特許番号
US05852010

反応ノート

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