Triethylamine → HCID 66769801, 화합물

HRID 660421노트

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HRID 660421 반응식
[C:1]([O:5][C:6](=[O:24])[NH:7][CH:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:9]([OH:16])[CH2:10][NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:32]([O:39][C:40](Cl)=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl.C([O-])([O-])=O.[Na+].[Na+]>[CH2:32]([O:39][C:40](=[O:41])[N:11]([CH2:10][CH:9]([OH:16])[CH:8]([NH:7][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:24])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:12][CH:13]([CH3:14])[CH3:15])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

참가 물질

6

반응물 3

HCID 8471Triethylamine2회HCID 10387Benzyl chloroformate2회HCID 21878363(1-Benzyl-2-hydroxy-3-isobutylaminopropyl)carbamic acid tert-butyl ester

생성물 1

HCID 66769801HCID 66769801, 화합물수율 100%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 10340Sodium Carbonate용매

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온도
-1.5 °C

실험 절차

(1-Benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid tert-butyl ester (2) (24.50 g, 72.80 mmol, 1 equiv) and triethylamine (7.37 g, 72.80 mmol, 1 equiv) were dissolved in dichloromethane (500 mL). The solution was cooled to −1.5° C., followed by the dropwise addition of benzylchloroformate (12.40 g, 72.80 mmol, 1 equiv). The solution was stirred at 0° C. for 24 h. Due to the incompleteness of the reaction, benzylchloroformate (2.40 g, 14.07 mmol) and triethylamine (1.44 g, 14.23 mmol) were added to the solution. The solution was stirred at room temperature for 24 h. The solution was diluted with 2% Na2CO3 solution (300 mL) and the mixture was stirred for 10 min. The organic layer was separated, washed with water (2×) and saturated sodium chloride solution (1×). The organic layer was dried on MgSO4, filtered, and evaporated to dryness to obtain the desired product as a yellow colored oil (34.30 g, 72.80 mmol, quantitative). LRMS (ES+): m/z 471 [M+H]+.

후처리

  1. additionwere added to the solution
  2. stirringThe solution was stirred at room temperature for 24 h
  3. stirringthe mixture was stirred for 10 min
  4. customThe organic layer was separated
  5. washwashed with water (2×) and saturated sodium chloride solution (1×)
  6. customThe organic layer was dried on MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness

출처 및 근거

ORD 기록
ord-497c0df08b2e47beafece6e6783189de
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084494B2

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