Sodium Iodide → N-(2-Acetylthio-3-methylbenzoyl)-N-cyclopentylglycine

HRID 325490ノート

反応式

HRID 325490 の反応式
C([O:5][C:6](=[O:27])[CH2:7][N:8]([C:14](=[O:26])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=1[S:22][C:23](=[O:25])[CH3:24])[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)(C)(C)C.[I-].[Na+].Cl[Si](C)(C)C>CC#N>[C:23]([S:22][C:16]1[C:17]([CH3:21])=[CH:18][CH:19]=[CH:20][C:15]=1[C:14]([N:8]([CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1)[CH2:7][C:6]([OH:27])=[O:5])=[O:26])(=[O:25])[CH3:24]

参加物

5

反応物 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 20465218N-(2-Acetylthio-3-methylbenzoyl)-N-cyclopentylglycine t-butyl ester

生成物 1

HCID 13298946N-(2-Acetylthio-3-methylbenzoyl)-N-cyclopentylglycine収率 100.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
55 °C

実験手順

N-(2-Acetylthio-3-methylbenzoyl)-N-cyclopentylglycine t-butyl ester (16.7 g, 0.047 mole) was dissolved in 100 ml CH3CN. Sodium iodide (9.6 g, 0.064 mole) was then added. The resulting slurry was covered with a nitrogen atmosphere and warmed slowly to 55° C. Chlorotrimethylsilane (6.9 g, 0.0641 mole) was then added in one portion. The reaction was stirred 30 minutes at 50°-55° C. The heat source was then removed and the reaction cooled to room temperature with an ice bath. Water (60 ml) and CH2Cl2 (100 ml) were then added. The reaction mixture was transferred to a separatory funnel and the aqueous layer quickly withdrawn. The organic was washed 2×50 ml H2O, 3×75 ml Na2S2O3, 2×100 ml brine, dried (MgSO4), filtered and concentrated in vacuo to give 15.9 g of an orange oil.

後処理

  1. customThe heat source was then removed
  2. temperaturethe reaction cooled to room temperature with an ice bath
  3. additionWater (60 ml) and CH2Cl2 (100 ml) were then added
  4. customThe reaction mixture was transferred to a separatory funnel
  5. customthe aqueous layer quickly withdrawn
  6. washThe organic was washed 2×50 ml H2O, 3×75 ml Na2S2O3, 2×100 ml brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-bb3538ecb35d459ba74123fa07b8e3a6
出典データセット
uspto-grants-1984_04
特許番号
US04440941

反応ノート

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