Water → [7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate

HRID 2383124ノート

反応式

HRID 2383124 の反応式
F.[C:2]([O:5][CH2:6][C:7]1[N:8]([CH2:28][C:29]([OH:32])([CH3:31])[CH3:30])[C:9]2[C:18]3[CH:17]=[CH:16][C:15]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:27]=1)(=[O:4])[CH3:3].C1C=C(Cl)C=C(C(OO)=[O:41])C=1.O>CN(C=O)C.CO>[C:2]([O:5][CH2:6][C:7]1[N:8]([CH2:28][C:29]([OH:32])([CH3:31])[CH3:30])[C:9]2[C:18]3[CH:17]=[CH:16][C:15]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:14][C:13]=3[N+:12]([O-:41])=[CH:11][C:10]=2[N:27]=1)(=[O:4])[CH3:3]

参加物

7

反応物 4

HCID 962WaterHCID 14917Hydrofluoric AcidHCID 70297m-Chloroperbenzoic acidHCID 67051092[7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate

生成物 1

HCID 67050977[7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate収率 100.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

Hydrogen fluoride (7.5 g of 48%, 0.18 mol) was added to a solution of [7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate (40.0 g, 0.0953 mol) in DMF (910 mL) and methanol (300 mL). mCPBA (60.6 g, 0.200 mol, 57% pure) was then added in one portion, and the reaction was stirred at ambient temperature for 5.5 hours. A mixture of ice and deionized water (4 L) was then added to the reaction mixture, and the resulting mixture was stirred vigorously for 30 minutes. The solid product was isolated by filtration, washed with deionized water, and dried under vacuum at 50° C. The solid was then triturated with diethyl ether (500 mL) for one hour, isolated by filtration, washed with diethyl ether (400 mL), and dried under vacuum at 40° C. to provide 41.7 g of [7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate.

後処理

  1. additionwas then added to the reaction mixture
  2. stirringthe resulting mixture was stirred vigorously for 30 minutes
  3. customThe solid product was isolated by filtration
  4. washwashed with deionized water
  5. customdried under vacuum at 50° C
  6. customThe solid was then triturated with diethyl ether (500 mL) for one hour
  7. customisolated by filtration
  8. washwashed with diethyl ether (400 mL)
  9. customdried under vacuum at 40° C.

出典と根拠

ORDレコード
ord-ebd121a6b9684eb5ae0415925f217bcb
出典データセット
uspto-grants-2012_09
特許番号
US08263594B2

反応ノート

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