tert-butyl 1-[[(2S)-1-[(Z)-1-aminoethylideneamino]oxy-3,3-dimethyl-1-oxobutan-2-yl]carbamoyl]-3-phenyl-6,8-dihydro-5H-imidazo[1,5-a]pyrazine-7-carboxylate → (S)-tert-butyl 1-(2,2-dimethyl-1-(3-methyl-1,2,4-oxadiazol-5-yl)propylcarbamoyl)-3-phenyl-5,6-dihydroimidazo[1,5-a]pyrazine-7(8H)-carboxylate

HRID 1971097ノート

反応式

HRID 1971097 の反応式
[NH2:1]/[C:2](=[N:4]\[O:5][C:6](=O)[C@@H:7]([NH:12][C:13]([C:15]1[N:16]=[C:17]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][C:19]=12)=[O:14])[C:8]([CH3:11])([CH3:10])[CH3:9])/[CH3:3]>CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>[CH3:10][C:8]([CH3:9])([CH3:11])[C@H:7]([NH:12][C:13]([C:15]1[N:16]=[C:17]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:20][C:19]=12)=[O:14])[C:6]1[O:5][N:4]=[C:2]([CH3:3])[N:1]=1

参加物

4

反応物 1

HCID 57635411tert-butyl 1-[[(2S)-1-[(Z)-1-aminoethylideneamino]oxy-3,3-dimethyl-1-oxobutan-2-yl]carbamoyl]-3-phenyl-6,8-dihydro-5H-imidazo[1,5-a]pyrazine-7-carboxylate

生成物 1

HCID 57635507(S)-tert-butyl 1-(2,2-dimethyl-1-(3-methyl-1,2,4-oxadiazol-5-yl)propylcarbamoyl)-3-phenyl-5,6-dihydroimidazo[1,5-a]pyrazine-7(8H)-carboxylate収率 88.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 2724141Tetrabutylammonium Fluoride溶媒

実験手順

Intermediate 22C (0.20 g, 0.39 mmol) was dissolved in a 1N solution of TBAF in THF (0.55 mL). The resulting mixture was stirred overnight, concentrated, diluted with EtOAc and washed successively with water and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by preparative flash chromatography on silica, eluting with a 20-70% ethyl acetate/hexanes gradient to provide Intermediate 22D (0.17 g, 88%). 1H-NMR (400 MHz, CDCl3-d) δ: 1.09 (s, 9H), 1.51 (s, 9H), 2.40 (s, 3H), 3.78 (m, 2H), 4.11 (m, 2H), 5.01 (m, 2H), 5.37 (d, 1H), 7.35 (m, 3H), 7.64 (m, 2H), 7.78 (d, 1H); LCMS (+ESI) m/z 495.1 [M+H]+.

後処理

  1. concentrationconcentrated
  2. additiondiluted with EtOAc
  3. washwashed successively with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative flash chromatography on silica
  8. washeluting with a 20-70% ethyl acetate/hexanes gradient

出典と根拠

ORDレコード
ord-e2ff82e0a122463c8c23e8d63861a19d
出典データセット
uspto-grants-2013_04
特許番号
US08431565B2

反応ノート

読み込み中…