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

HRID 1382922ノート

反応式

HRID 1382922 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4a05b7548a7f41168306cee0dc435ebb
出典データセット
uspto-grants-1989_02
特許番号
US04808605

反応ノート

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