Ammonium cerium (IV) nitrate → 5,6,7,8-tetrahydro-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-one

HRID 1529567ノート

反応式

HRID 1529567 の反応式
[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.COC1C=CC(C[N:32]2[CH2:38][CH2:37][CH2:36][C:35]3[N:39]=[C:40]([CH2:42][O:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[S:41][C:34]=3[C:33]2=[O:50])=CC=1>O.C(#N)C>[O:43]([CH2:42][C:40]1[S:41][C:34]2[C:33](=[O:50])[NH:32][CH2:38][CH2:37][CH2:36][C:35]=2[N:39]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

参加物

5

反応物 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 666085925,6,7,8-tetrahydro-5-[(4-methoxyphenyl)methyl]-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-one

生成物 1

HCID 532467235,6,7,8-tetrahydro-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-one収率 52.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

実験手順

A solution of ammonium cerium (IV) nitrate (1.08 g, 1.97 mmol) in H2O (1.5 mL) was added to a stirred solution of 5,6,7,8-tetrahydro-5-[(4-methoxyphenyl)methyl]-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-one (0.22 g, 0.56 mmol) in ACN (5 mL). The mixture was stirred at room temperature for 16 hours and then diluted with H2O and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 100/0). The desired fractions were collected and the solvents evaporated in vacuo to yield 5,6,7,8-tetrahydro-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-one (0.081 g, 52%) as a white solid. C14H14N2O2S LCMS: Rt 1.59, m/z 275 [M+H]+ (using method, LC-MS Method 6).

後処理

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 100/0)
  7. customThe desired fractions were collected
  8. customthe solvents evaporated in vacuo

出典と根拠

ORDレコード
ord-a69ab4acb9164ad68c63f9e85a9d469f
出典データセット
uspto-grants-2015_07
特許番号
US09090632B2

反応ノート

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