Hydrogen Peroxide → tert-Butyl-4-({[4-(2-butynyloxy)phenyl]sulfinyl}methyl)-4-[(hydroxyamino)carbonyl]-1-piperidinecarboxylate

HRID 353555ノート

反応式

HRID 353555 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:18][S:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]#[C:29][CH3:30])=[CH:22][CH:21]=2)([C:14]([NH:16][OH:17])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:31]O>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:18][S:19]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]#[C:29][CH3:30])=[CH:22][CH:21]=2)=[O:31])([C:14]([NH:16][OH:17])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 784Hydrogen PeroxideHCID 23513813Tert-butyl-4-({[4-(2-butynyloxy)phenyl]sulfanyl)methyl)-4-[(hydroxyamino)carbonyl]-1-piperidinecarboxylate

生成物 1

HCID 23513828tert-Butyl-4-({[4-(2-butynyloxy)phenyl]sulfinyl}methyl)-4-[(hydroxyamino)carbonyl]-1-piperidinecarboxylate収率 67%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a slurry of tert-butyl-4-({[4-(2-butynyloxy)phenyl]sulfanyl}methyl)-4-[(hydroxyamino) carbonyl]-1-piperidinecarboxylate (0.24 g, 0.55 mmol) at 0° C. in 7 mL of MeOH was added dropwise 3.5 mL of 30% hydrogen peroxide. The reaction was allowed to warm to room temperature and stirred for 18 h. The reaction was cooled to 0° C. and quenched with 3.5 mL of a saturated solution of Na2SO3. The organaics were removed and the aqueous solution was extracted with CH2Cl2. The organics were washed with H2O, brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with ether to provide 0.166 g (67%) of the desired product as an off white solid. Electrospray Mass Spec: 451.3 (M+H)+.

後処理

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with 3.5 mL of a saturated solution of Na2SO3
  3. customThe organaics were removed
  4. extractionthe aqueous solution was extracted with CH2Cl2
  5. washThe organics were washed with H2O, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with ether

出典と根拠

ORDレコード
ord-f9ec373b40784bd0a92d8e98a477e78c
出典データセット
uspto-grants-2004_06
特許番号
US06753337B2

反応ノート

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