N-BOC-ethylenediamine → HCID 54501153, compound

HRID 1590895Notes

Reaction equation

HRID 1590895 reaction equation
[C:1]1([C:7]2[C:8]([C:12]([O:14]CC)=O)=[N:9][O:10][CH:11]=2)[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:1]1([C:7]2[C:8]([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])=[N:9][O:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 187201N-BOC-ethylenediamineHCID 13449587HCID 13449587, compound

Product 1

HCID 54501153HCID 54501153, compoundYield 84.1%

Procedure

3.9 g (17.95 mmol) of ethyl 4-phenyl-3-isoxazolecarboxylate and 5.8 g (36.2 mmol) of t-butyl (2-aminoethyl)carbamate were heated together to 110° for 2 hours under reduced pressure. Chromatography on silica gel and elution with methylene chloride which contained 5% and, respectively, 10% of ethyl acetate yielded an oil which crystallized from ethyl acetate/hexane. In this manner there were obtained 5.0 g (84%) of t-butyl [2-(4-phenyl-3-isoxazolecarboxamido)ethyl]carbamate as white crystals, melting point 170°-171°.

Workup

  1. washChromatography on silica gel and elution with methylene chloride which
  2. customrespectively, 10% of ethyl acetate yielded an oil which
  3. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-3d322cf9bb2a40839bf13656b161048e
Source dataset
uspto-grants-1993_04
Patent number
US05204482

Reaction notes

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