Triethylamine → N-(3-Acetylthio-2-methylpropanoyl)-N-cyclobutylglycine t-butyl ester

HRID 127615노트

반응식

HRID 127615 반응식
[C:1]([O:5][C:6](=[O:13])[CH2:7][NH:8][CH:9]1[CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:21]([S:24][CH2:25][CH:26]([CH3:30])[C:27](Cl)=[O:28])(=[O:23])[CH3:22]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:13])[CH2:7][N:8]([C:27](=[O:28])[CH:26]([CH3:30])[CH2:25][S:24][C:21](=[O:23])[CH3:22])[CH:9]1[CH2:10][CH2:11][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 20285462HCID 20285462, 화합물

생성물 1

HCID 20285461N-(3-Acetylthio-2-methylpropanoyl)-N-cyclobutylglycine t-butyl ester수율 72%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a chilled (0.5° C.) methylene chloride solution of N-cyclobutyl-glycine t-butyl ester (63.2 g, 0.34 mol) and triethylamine (26 g, 0.4 mol) was added dropwise 3-acetylthio-2-methylpropanoyl chloride (61.4 g, 0.34 mol). After stirring overnight the reaction mixture was filtered and the filtrate was concentrated. The residue was redissolved in ethyl acetate, washed with 5% HCl (3×500 ml), brine (500 ml) and saturated aqueous sodium bicarbonate (6×600 ml), dried over MgSO4, filtered, and concentrated yielding 80.6 g (72%) of the product as a brown oil.

후처리

  1. filtrationwas filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was redissolved in ethyl acetate
  4. washwashed with 5% HCl (3×500 ml), brine (500 ml) and saturated aqueous sodium bicarbonate (6×600 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-df8ba9e0861446908f0ad3eb723bd1b3
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04256761

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