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

HRID 1382922Notes

Reaction equation

HRID 1382922 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4a05b7548a7f41168306cee0dc435ebb
Source dataset
uspto-grants-1989_02
Patent number
US04808605

Reaction notes

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