Triethylamine → Benzyl [3-(2-benzthiazolyl)propyl]methylcarbamate

HRID 1382922노트

반응식

HRID 1382922 반응식
[CH2:1]([O:8][C:9]([N:11]([CH2:13][CH2:14][CH2:15][C:16](O)=O)[CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[NH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[SH:41]>O1CCCC1.O>[S:41]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:16]1[CH2:15][CH2:14][CH2:13][N:11]([CH3:12])[C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 87132-AminothiophenolHCID 62365Isobutyl chloroformateHCID 190283044-(((Benzyloxy)carbonyl)(methyl)amino)butanoic acid

생성물 1

HCID 53819401Benzyl [3-(2-benzthiazolyl)propyl]methylcarbamate수율 25.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

5.0 g (19.9 mmol) of 4-[1-(benzyloxy)-N-methylformamido]butyric acid are dissolved in 175 ml of tetrahydrofuran. To the solution, cooled to -20°, are added 2.95 ml (2.1 g; 24 mmol) of triethylamine and 2.95 ml (22 mmol) of isobutyl chloroformate. The reaction mixture is thereafter stirred at this temperature for 1 hour. 2.45 g (19.6 mmol) of 2-aminothiophenol are then added and the reaction mixture is stirred at room temperature for 20 hours. Thereupon, 250 ml of water are added and the mixture is extracted with ethyl acetate. The organic phase is dried over magnesium sulphate and evaporated under reduced pressure. After chromatography on silica gel using a 1:1 mixture of ethyl acetate and hexane there are obtained 1.7 g (25.1%) of benzyl [3-(2-benzthiazolyl)propyl]methylcarbamate as an oil, MS: M+ 340.

후처리

  1. temperatureTo the solution, cooled to -20°
  2. stirringthe reaction mixture is stirred at room temperature for 20 hours
  3. extractionthe mixture is extracted with ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customevaporated under reduced pressure
  6. additionAfter chromatography on silica gel using a 1:1 mixture of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-4a05b7548a7f41168306cee0dc435ebb
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04808605

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