Triethylsilane → 3-[(4-Hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)-amino]-5-iodo-thiophene-2-carbox

HRID 1046447ノート

反応式

HRID 1046447 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([I:27])=[CH:8][C:9]=1[N:10]([C:18]([CH:20]1[CH2:25][CH2:24][CH:23]([CH3:26])[CH2:22][CH2:21]1)=[O:19])[CH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)=[O:4].C[Si](C)(C)OC1CCOC1.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>[N+](C)([O-])=O.CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([I:27])=[CH:8][C:9]=1[N:10]([CH:11]1[CH2:12][CH2:13][CH:14]([OH:17])[CH2:15][CH2:16]1)[C:18]([CH:20]1[CH2:21][CH2:22][CH:23]([CH3:26])[CH2:24][CH2:25]1)=[O:19])=[O:4]

参加物

7

反応物 4

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 581141515-Iodo-3-[(4-methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl esterHCID 66849751Trimethyl-(tetrahydro-furan-3-yloxy)-silane

生成物 1

HCID 249893473-[(4-Hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)-amino]-5-iodo-thiophene-2-carbox収率 50.7%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6375Nitromethane溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 5-iodo-3-[(4-methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester (2.5 g, 4.96 mmol) and FeCl3 (41 mg, 0.252 mmol) in nitromethane (15.0 mL) cooled to 0° C. was added neat trimethyl-(tetrahydro-furan-3-yloxy)-silane (955 mg, 5.95 mmol) followed by the dropwise addition of triethylsilane (0.947 mL, 5.92 mmol). The reaction was allowed to slowly warm to room temperature and stirred overnight. Sat. NaHCO3 was added and the reaction mixture was extracted with dichloromethane. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give a solid. The crude solid was heated in methanol, cooled and collected by filtration to provide 3-[(4-hydroxy-cyclohexyl)-(4-methyl-cyclohexanecarbonyl)-amino]-5-iodo-thiophene-2-carboxylic acid methyl ester (1.27 g, 44%) as a colorless solid.

後処理

  1. temperatureto slowly warm to room temperature
  2. extractionthe reaction mixture was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a solid
  7. temperaturecooled
  8. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-272856e64a3b4111a1792c77d4fe2078
出典データセット
uspto-grants-2013_10
特許番号
US08569302B2

反応ノート

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