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

HRID 1254322노트

반응식

HRID 1254322 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 3283Diethyl Ether용매2회

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온도
62.5 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-fe89ea90939c4dfdbfe428488c8a9aa7
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455521B2

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