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

HRID 325490노트

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HRID 325490 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
55 °C

실험 절차

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 The reaction mixture was transferred to a separatory funnel and the aqueous layer quickly withdrawn.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.

후처리

  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 customthe aqueous layer quickly withdrawn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

출처 및 근거

ORD 기록
ord-bb3538ecb35d459ba74123fa07b8e3a6
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04440941

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