N-BOC-ethylenediamine → t-Butyl [2-(5-phenyl-4-thiazolecarboxamido)ethyl]carbamate

HRID 1085824Notes

Reaction equation

HRID 1085824 reaction equation
[C:1]1([C:7]2[S:11][CH:10]=[N:9][C:8]=2[C:12]([O:14]CC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]>C(O)C>[C:1]1([C:7]2[S:11][CH:10]=[N:9][C:8]=2[C:12]([NH:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 187201N-BOC-ethylenediamineHCID 12300673Ethyl 5-phenylthiazole-4-carboxylate

Product 1

HCID 53676915t-Butyl [2-(5-phenyl-4-thiazolecarboxamido)ethyl]carbamateYield 60.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.8 g (20.58 mmol) of ethyl 5-phenyl-4-thiazolecarboxylate and 4.0 g (25.0 mmol) of t-butyl (2-aminoethyl)carbamate were heated under reduced pressure for 21 hours at a bath temperature of 100°, whereby the ethanol formed was distilled off continuously. Subsequently the mixture was cooled, dissolved in 50 ml of methylene chloride and chromatographed on 150 g of silica gel. Elution was first carried out with methylene chloride, then with a 9:1, 8:2 and finally 7:3 mixture of methylene chloride and ethyl acetate. The fractions which were pure according to the thin-layer chromatogram were combined and recrystallized from ethyl acetate/hexane. In this manner there were obtained 4.3 g (60.1%) of t-butyl [2-(5-phenyl-4-thiazolecarboxamido)ethyl]carbamate as white crystals, melting point 139-140°.

Workup

  1. customformed
  2. distillationwas distilled off continuously
  3. temperatureSubsequently the mixture was cooled
  4. dissolutiondissolved in 50 ml of methylene chloride
  5. customchromatographed on 150 g of silica gel
  6. washElution
  7. additionwith a 9:1, 8:2 and finally 7:3 mixture of methylene chloride and ethyl acetate
  8. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d97e4e3c646c43d582201a7b9eee806d
Source dataset
uspto-grants-1991_04
Patent number
US05011849

Reaction notes

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