Reaction #487580

ord-44912896e827440ca1aa571c5410d735

Reaction equation

CCOC(=O)CCN(CC(=O)OCC)C(=O)CCCCCNC(=O)OCC1c2ccccc2-c2ccccc21
3-{Ethoxycarbonylmethyl-[6-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoyl]-amino}-propionic acid ethyl ester
CCOC(=O)CCN(CC(=O)OCC)C(=O)CCCCCN
3-[(6-Amino-hexanoyl)-ethoxycarbonylmethyl-amino]-propionic acid ethyl ester

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationThe reaction mixture was concentrated under vacuum, water
  2. 2
    workup.ADDITIONwas added to the residue
  3. 3
    Extractionthe product was extracted with ethyl acetate
  4. 4
    OtherThe crude product was purified by conversion into its hydrochloride salt

Procedure

3-{Ethoxycarbonylmethyl-[6-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoyl]-amino}-propionic acid ethyl ester AB (11.5 g, 21.3 mmol) was dissolved in 20% piperidine in dimethylformamide at 0° C. The solution was continued stirring for 1 h. The reaction mixture was concentrated under vacuum, water was added to the residue, and the product was extracted with ethyl acetate. The crude product was purified by conversion into its hydrochloride salt.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08741866B2uspto-grants-2014_06