p-Toluenesulfonic acid monohydrate → 1-(3-amino-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propyl)cyclohexanol

HRID 1254322ノート

反応式

HRID 1254322 の反応式
CC1C=CC(S(O)(=O)=O)=CC=1.O.C(OC([NH:20][CH2:21][CH:22]([N:31]([CH3:41])[C:32]([O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])=[O:33])[CH2:23][C:24]1([OH:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=O)(C)(C)C>C(O)C.CCOCC>[NH2:20][CH2:21][CH:22]([N:31]([CH3:41])[C:32]([O:34][CH2:35][CH2:36][Si:37]([CH3:38])([CH3:40])[CH3:39])=[O:33])[CH2:23][C:24]1([OH:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

参加物

5

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 671883231-(3-(t-butoxy-carbonylamino)-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propyl)cyclohexanol

生成物 1

HCID 671900581-(3-amino-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propyl)cyclohexanol収率 108.4%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
62.5 °C

実験手順

A solution of p-TsOH.H2O (25 mg) in ethanol (0.5 mL) was added to 1-(3-(t-butoxy-carbonylamino)-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propyl)cyclohexanol (50 mg, 0.12 mmol) dissolved in ether (12 mL). The transfer was completed with additional ether (2 mL). The resulting solution was evaporated under reduced pressure at rt to remove Et2O and heated at 60-65° C. for 20 min under reduced pressure to remove ethanol. The residue was dissolved in MeOH and aqueous K2CO3 was added. The mixture was evaporated and extracted with EtOAc (3×). The combined organic phases were dried over Na2SO4, filtered and evaporated to give 1-(3-amino-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)-amino)propyl)cyclohexanol (43 mg, 89%). MS m/z 453 (M+Na+).

後処理

  1. customThe resulting solution was evaporated under reduced pressure at rt
  2. customto remove Et2O
  3. customto remove ethanol
  4. dissolutionThe residue was dissolved in MeOH
  5. additionaqueous K2CO3 was added
  6. customThe mixture was evaporated
  7. extractionextracted with EtOAc (3×)
  8. dry with materialThe combined organic phases were dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated

出典と根拠

ORDレコード
ord-fe89ea90939c4dfdbfe428488c8a9aa7
出典データセット
uspto-grants-2013_06
特許番号
US08455521B2

反応ノート

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