tert-Butyl {3-[4-cyano-2-dimethylcarbamoyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl]cyclopent-2-enyl}methylcarbamate → HCID 68585497、化合物

HRID 17626

反応式

HRID 17626 の反応式
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C:12](=[O:16])[N:13]([CH3:15])[CH3:14])[O:11][C:7]=2[C:6]([C:17]2[CH2:21]C[CH:19]([CH2:22][NH:23][C:24](=O)OC(C)(C)C)[CH:18]=2)=[C:5]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:4]=1[CH3:37])#[N:2]>Cl.O1CCOCC1>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C:12]([N:13]([CH3:15])[CH3:14])=[O:16])[O:11][C:7]=2[C:6]([CH:17]2[CH2:18][CH2:19][C:22]([NH:23][CH3:24])=[CH:21]2)=[C:5]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:4]=1[CH3:37])#[N:2]

参加物

3

反応物 1

HCID 86630887tert-Butyl {3-[4-cyano-2-dimethylcarbamoyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl]cyclopent-2-enyl}methylcarbamate

生成物 1

HCID 68585497HCID 68585497、化合物収率 55.5%

試薬・触媒・溶媒 1

HCID 204431481,4-Dioxane hydrochloride溶媒

実験手順

tert-Butyl {3-[4-cyano-2-dimethylcarbamoyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl]cyclopent-2-enyl}methylcarbamate (I-340-1) (134 mg, 0.27 mmol) was dissolved in 4 N hydrochloric acid/1,4-dioxane solution (3 ml), and stirred at room temperature for 2 hours. The solvent was evaporated away under reduced pressure, then ethanol was added to the resulting residue, followed by concentration under reduced pressure. This operation was repeated once again. The residue was dissolved in chloroform (15 ml) and an aqueous saturated sodium hydrogencarbonate solution (15 ml), and vigorously stirred for 10 minutes. The aqueous layer was separated, extracted twice with chloroform. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:7 N ammonia-containing methanol solution=93:7, v/v) to obtain a roughly-purified product (60 mg). This was further purified by preparative TLC (eluent, chloroform:methanol=9:1, v/v) to obtain a brown solid (50 mg). The solid was washed in slurry with diisopropyl ether, and a pale brown solid was collected by filtration. The solid was dried at 60° C. under reduced pressure for 48 hours to obtain the entitled compound (42 mg, 39%).

後処理

  1. customThe solvent was evaporated away under reduced pressure
  2. additionethanol was added to the resulting residue
  3. concentrationfollowed by concentration under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform (15 ml)
  5. stirringan aqueous saturated sodium hydrogencarbonate solution (15 ml), and vigorously stirred for 10 minutes
  6. customThe aqueous layer was separated
  7. extractionextracted twice with chloroform
  8. washwashed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe insoluble matter was separated by filtration
  11. customthe solvent was evaporated away
  12. customthe resulting residue was purified by preparative TLC (eluent, chloroform
  13. addition7 N ammonia-containing methanol solution=93:7

出典と根拠

ORDレコード
ord-89cca707b44241718854f8610b37a1bd
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

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