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Acetic Acid → 4-[5-Amino-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]cyclohex-3-en-1-one

HRID 1959443
ノート
印刷プレビュー

反応式

HRID 1959443 の反応式
C(OC([N:8]([C:16]1[C:21]([C:22]2[O:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:25][N:26]=2)=[N:20][C:19]([C:33]2[CH2:42][CH2:41][C:36]3(OCC[O:37]3)[CH2:35][CH:34]=2)=[CH:18][N:17]=1)C(=O)OC(C)(C)C)=O)(C)(C)C.CC(O)=O.O.[OH-].[Na+]>CCOC(C)=O>[NH2:8][C:16]1[N:17]=[CH:18][C:19]([C:33]2[CH2:42][CH2:41][C:36](=[O:37])[CH2:35][CH:34]=2)=[N:20][C:21]=1[C:22]1[O:23][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:25][N:26]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 66744206tert-butyl N-tert-butoxycarbonyl-N-[5-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]carbamate

生成物 1

HCID 667447634-[5-Amino-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]cyclohex-3-en-1-one収率 82%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A solution of tert-butyl N-tert-butoxycarbonyl-N-[5-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]carbamate in (40 mg, 0.069 mmol) AcOH (832 mg, 788 μL, 13.85 mmol) and H2O (50 mg, 50 μL, 2.8 mmol) was heated at 80° C. for 2 h. The reaction mixture was diluted with 10 ml of EtOAc and pH was adjusted to 8 with 1N NaOH. The reaction mixture was washed with 20 ml of NaHCO3. The layers were separated and the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to obtain 4-[5-amino-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]cyclohex-3-en-1-one (19 mg, 82%), which was used as crude for the next step. LC/MS m/z 334.0 [M+H]+.

後処理

  1. washThe reaction mixture was washed with 20 ml of NaHCO3
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-7c36baa8898d43be85d0a2108ca411ed
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08410112B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート