Hydroxylamine → HCID 87348653、化合物

HRID 61492ノート

反応式

HRID 61492 の反応式
[CH2:1]([C@:8]12[CH2:16][C@H:12]([C:13](=[O:15])[O:14]1)[C@@H:11]([C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:21][CH2:20]1)=[O:18])[CH2:10][CH2:9]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:31][OH:32]>CO>[CH2:1]([C@@:8]1([OH:14])[CH2:16][C@H:12]([C:13]([NH:31][OH:32])=[O:15])[C@@H:11]([C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)=[O:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 787HydroxylamineHCID 67304651HCID 67304651、化合物

生成物 1

HCID 87348653HCID 87348653、化合物収率 26%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a stirred solution of (1S,2S,5S)-5-benzyl-2-[(4-phenylpiperazin-1-yl)carbonyl]-6-oxabicyclo[3.2.1]-octan-7-one (8.0 mg, 0.020 mmol) in anhydrous methanol (1.0 mL, 0.025 mol) at rt was added 1.50 M of hydroxylamine in methanol (0.396 mL). The reaction mixture was stirred at rt for 3 h. The reaction was quenched with saturated aqueous NH4Cl (15 mL), extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC with 5-95% MeCN/H2O (with 0.05% TFA) to give the pure product as a colorless solid (2.3 mg, 26% in yield). MS (ESI): (M+H)+=438.1.

後処理

  1. customThe reaction was quenched with saturated aqueous NH4Cl (15 mL)
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by reverse phase HPLC with 5-95% MeCN/H2O (with 0.05% TFA)

出典と根拠

ORDレコード
ord-a84c64821f634b04b8f6e33e9767a318
出典データセット
uspto-grants-2016_09
特許番号
US09440958B2

反応ノート

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