Reacción #10519

ord-0671b17e79594082bfe04925787d737d

Ecuación de reacción

CC(C)(C)OC(=O)N1[C@H](CC(NCc2ccccc2)C(=O)O)CC[C@H]1C(=O)O
(2S,5S)-5-(2-benzylamino-2-carboxyethyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
[H][H]
hydrogen
CC(=O)O.CC(C)(C)OC(=O)N1[C@H](CC(N)C(=O)O)CC[C@H]1C(=O)O
(2S,5S)-5-(2-amino-2-carboxyethyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester hydrogen acetate

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    FiltraciónThe catalyst was filtered off through kieselguhr
  2. 2
    Lavadothe filter cake was washed with 20 ml of acetic acid
  3. 3
    ConcentraciónThe combined organic phases were concentrated in vacuo
  4. 4
    OtroThe crude product was employed without further purification in the next reaction

Procedimiento

1600 mg of (2S,5S)-5-(2-benzylamino-2-carboxyethyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester were dissolved in 30 ml of acetic acid. 100 mg of 20% palladium hydroxide on activated carbon were added thereto, and the mixture was hydrogenated under an atmosphere of 1 bar of hydrogen for 1 h. Ar was then passed over the solution for 10 min. The catalyst was filtered off through kieselguhr and the filter cake was washed with 20 ml of acetic acid. The combined organic phases were concentrated in vacuo. The crude product was employed without further purification in the next reaction.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07094800B2uspto-grants-2006_08