Triethylamine → Ethyl N-{4-[{3-([tert-butoxycarbonyl)(methyl)amino]propyl}(methyl)carbamoyl]phenyl}-beta-alaninate

HRID 446603

반응식

HRID 446603 반응식
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][NH:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[CH3:2].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[CH3:32][N:33]([CH2:41][CH2:42][CH2:43][NH:44][CH3:45])[C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(OCC)(=O)C>[C:36]([O:35][C:34]([N:33]([CH3:32])[CH2:41][CH2:42][CH2:43][N:44]([CH3:45])[C:12]([C:11]1[CH:10]=[CH:9][C:8]([NH:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:17])=[CH:16][CH:15]=1)=[O:14])=[O:40])([CH3:39])([CH3:38])[CH3:37]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 17868293tert-butyl N-methyl-N-(3-(methylamino)propyl)carbamateHCID 21830455Ethyl 3-[4-(carboxy)phenylamino]propionate

생성물 1

HCID 66793768Ethyl N-{4-[{3-([tert-butoxycarbonyl)(methyl)amino]propyl}(methyl)carbamoyl]phenyl}-beta-alaninate수율 89%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

4-[(3-Ethoxy-3-oxopropyl)amino]benzoic acid (200 mg, 0.84 mmol) (U.S. Pat. No. 5,977,101 A1) was dissolved in methylene chloride (6 mL), triethylamine (0.14 mL, 1.01 mmol) and pivaloyl chloride (0.10 mL, 0.84 mmol) were added under ice cooling, and the mixture was stirred at the same temperature under a nitrogen atmosphere for 15 minutes. Subsequently, a solution of tert-butyl methyl[3-(methylamino)propyl]carbamate (179 mg, 0.89 mmol) in methylene chloride (2 mL) was added under ice cooling, and the mixture was stirred at room temperature under a nitrogen atmosphere for 16 hours. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate, 1:9, v/v) to give the title compound (315 mg; yield, 89%) as a light yellow oily substance.

후처리

  1. stirringthe mixture was stirred at room temperature under a nitrogen atmosphere for 16 hours
  2. customto separate the layers
  3. customThe resulting organic layer was separated
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate, 1:9, v/v)

출처 및 근거

ORD 기록
ord-c58b11a35cee4c7bbece2da914d4954f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476253B2

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