1,4-Dioxane → benzyl (4S,7S)-4-(5-(4-bromophenyl)-1H-imidazol-2-yl)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepin-7-ylcarbamate

HRID 709374ノート

反応式

HRID 709374 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][NH:10][C:11]([C@H:13]2[N:18]3[C:19](=[O:36])[C@@H:20]([NH:25][C:26](=[O:35])[O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:21][CH2:22][C:23](=[O:24])[N:17]3[CH2:16][CH2:15][CH2:14]2)=O)=[CH:4][CH:3]=1.O1CCOCC1.C([O-])(=O)C.[NH4+:48]>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:48][C:11]([C@H:13]3[N:18]4[C:19](=[O:36])[C@@H:20]([NH:25][C:26](=[O:35])[O:27][CH2:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH2:21][CH2:22][C:23](=[O:24])[N:17]4[CH2:16][CH2:15][CH2:14]3)=[N:10][CH:9]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 312751,4-DioxaneHCID 517165Ammonium AcetateHCID 131733894benzyl (4S,7S)-4-(2-(4-bromophenyl)-2-oxoethylcarbamoyl)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepin-7-ylcarbamate

生成物 1

HCID 89510323benzyl (4S,7S)-4-(5-(4-bromophenyl)-1H-imidazol-2-yl)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepin-7-ylcarbamate収率 34.1%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

In a 10 ml, seal tube, benzyl (4S,7S)-4-(2-(4-bromophenyl)-2-oxoethylcarbamoyl)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepin-7-ylcarbamate (200 mg, 350 μmol) was combined with 1,4-dioxane (5 ml) to give a light yellow solution. Ammonium acetate (270 mg, 3.5 mmol) was added and the reaction mixture was heated at 110° C. for 12 hr. It was cooled and diluted with EtOAc (2×30 ml). The combined organic layers were washed with brine and H2O, dried with MgSO4 and concentrated in vacuo to afford a viscous oil. The crude was purified on a silica gel column (CH2Cl2, 2%, 4%, 6%, 8% MeOH/CH2Cl2) to afford benzyl (4S,7S)-4-(5-(4-bromophenyl)-1H-imidazol-2-yl)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepin-7-ylcarbamate as a yellow solid (66 mg, 34.1%). ESI-LRMS m/e calcd for C26H26BrN5O4 [M+] 552. found 553 [M+H+].

後処理

  1. customIn a 10 ml, seal tube
  2. customto give a light yellow solution
  3. temperatureIt was cooled
  4. washThe combined organic layers were washed with brine and H2O
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo
  7. customto afford a viscous oil
  8. customThe crude was purified on a silica gel column (CH2Cl2, 2%, 4%, 6%, 8% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-1c7f8c584c944adaa429b3b9631b55b5
出典データセット
uspto-grants-2015_11
特許番号
US09180193B2

反応ノート

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