Water → 1-(tert-Butoxycarbonyl)-3-[(4-phenylthiazol-2-yl)thiomethyl]piperidine

HRID 602184ノート

反応式

HRID 602184 の反応式
[SH:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.C(=O)([O-])[O-].[K+].[K+].[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH2:29][CH:28]([CH2:32]I)[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].O>CN(C)C=O>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH2:29][CH:28]([CH2:32][S:1][C:2]2[S:3][CH:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:6]=2)[CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 20716152Tert-butyl 3-(iodomethyl)piperidine-1-carboxylateHCID 1785278304-phenyl-1,3-thiazole-2-thiol

生成物 1

HCID 589926811-(tert-Butoxycarbonyl)-3-[(4-phenylthiazol-2-yl)thiomethyl]piperidine収率 99.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Mercapto-4-phenylthiazole (304 mg, 1.54 mmol) and potassium carbonate (261 mg, 1.85 mmol) were added to 1-(tert-butoxycarbonyl)-3-iodomethylpiperidine (500 mg, 1.54 mmol) in N,N-dimethylformamide (5 mL). The mixture was stirred at room temperature for 30 min. Subsequently, water was added and the mixture was extracted with ethyl acetate. The extract was then washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=40:1->10:1) gave 598 mg (99%) of the desired compound as a colorless oil.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was then washed with brine
  3. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  4. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=40:1->10:1)

出典と根拠

ORDレコード
ord-46c54148ff874ad0bba0413cd58654ad
出典データセット
uspto-grants-2011_03
特許番号
US07902367B2

反応ノート

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