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Ammonium Hydroxide → 2-(N'-n-butylureido)-5-methylsulfinyl-N-[(1-diphenylmethylpiperidin-4yl)methyl]benzamide

HRID 362938
ノート
印刷プレビュー

反応式

HRID 362938 の反応式
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([NH:32][C:33]([NH:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:34])=[C:7]([CH:31]=1)[C:8]([NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)=[O:9].[OH:40]OS([O-])=O.[K+].[NH4+].[OH-]>CC#N.C(Cl)Cl.CO.O.C(Cl)Cl>[CH2:36]([NH:35][C:33](=[O:34])[NH:32][C:6]1[CH:5]=[CH:4][C:3]([S:2]([CH3:1])=[O:40])=[CH:31][C:7]=1[C:8]([NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:14][CH2:13]1)=[O:9])[CH2:37][CH2:38][CH3:39]
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 3

HCID 14923Ammonium HydroxideHCID 23707502Potassium hydroxy sulfite2 回HCID 675956385-methylthio-2-(N'-n-butylureido)-N-[(1-diphenylme-thylpiperidin-4-yl)methyl]benzamide

生成物 1

HCID 675954132-(N'-n-butylureido)-5-methylsulfinyl-N-[(1-diphenylmethylpiperidin-4yl)methyl]benzamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane
溶媒
HCID 86753736HCID 86753736、化合物溶媒

実験手順

A solution of 5-methylthio-2-(N'-n-butylureido)-N-[(1-diphenylme-thylpiperidin-4-yl)methyl]benzamide (EXAMPLE 73) (200 mg, 0.367 mmol) in CH3CN/CH2Cl2 /MeOH/H2O (10 ml/2 ml/4 ml/0.5 ml) was agitated with OXONE® (2KHSO5KHSO4K2SO4) (142 mg, 0.231 mmol) for 2 hours at room temperature and then an additional OXONE® (15 mg) was added. The reaction mixture was made basic with 25% NH4OH and diluted with CH2Cl2. The organic layer was washed twice with H2O, dried over MgSO4 and evaporated. The residue was purified by column chromatography on silica gel to give 2-(N'-n-butylureido)-5-methylsulfinyl-N-[(1-diphenylmethylpiperidin-4yl)methyl]benzamide. 130 mg (63%): mp 209°-211° C.; 1H NMR (CDCl3) ppm: 0.91 (3H, t), 1.33-1.88 (11H, m), 2.69 (3H, s), 2.88 (2H, m), 3.22-3.31 (4H, m), 4.24 (1H, s), 4.85 (1H, bt), 7.03 (1H, bt), 7.13-7.42 (11H, m), 7.91 (1H, d), 8.63 (1H, d), 10.71 (1H, s); and 2-(N'-n-butylureido)-5-methylsulfonyl-N-[(1-diphenylmethylpiperidin-4-yl)-methyl]benzamide, 30 mg (14%): mp 178°-179° C.; 1H NMR (CDCl3) ppm: 0.93(3H, t), 1.31-1.88 (11H, m), 2.90 (2.90 (2H, m), 3.02 (3H, s), 3.23-3.34 (4H, m), 4.25 (1H, s), 4.79 (1H, bt), 6.61 (1H, bt), 7.13-7.40 (10H, m), 7.89 (1H, dd), 7.97 (1H, d), 8.73 (1H, d), 10.82 (1H, s), respectively.

後処理

  1. washThe organic layer was washed twice with H2O
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-8fd449b5d86f4c1c8b58d9037c8142e3
出典データセット
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05872115

反応ノート

読み込み中…

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