Reacción #63422

ord-3dd2675b0d0549adad9407b00880dd04

Ecuación de reacción

CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O
N(tert-butyloxycarbonyl)-L-phenylalanine
CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O
N-(tert-butyloxycarbonyl)-L-leucine
CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O
N-(tert-butyloxycarbonyl)-L-phenylalanine
CC(C)N=C=NC(C)C
N,N-diisopropylcarbodiimide
CC(C)C[C@H](N)C(=O)O
leucine
O=C(O)C(F)(F)F
trifluoroacetic acid
CC(C)C[C@H](N)C(=O)O
leucine
CC(C)C[C@H](N)C(=O)O
L-leucine
N[C@@H](Cc1ccccc1)C(=O)O
L-phenylalanine

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadothe resin was washed three times with methylene chloride
  2. 2
    Otrodried under vacuum

Procedimiento

A dipeptide of L-leucine and L-phenylalanine was prepared using the above described resin. N-(tert-butyloxycarbonyl)-L-leucine was coupled using the procedure of Example 1. Amino acid analysis of this resin showed a leucine content of 0.75 meq/g. When treated with 45% trifluoroacetic acid to deprotect and cap the residual sulfide as in Example 1, the leucine content dropped to 0.49 meq/g. A sample of this resin (0.994 g, 0.49 mmol) was washed twice with a solution of 10% diisopropyl ethylamine in methylene chloride, followed by three washes with methylene chloride to neutralize the resin. The resin was coupled with N(tert-butyloxycarbonyl)-L-phenylalanine by suspending the resin in 10 ml methylene chloride and adding 464 mg (1.75 mmol) N-(tert-butyloxycarbonyl)-L-phenylalanine and 0.27 ml (235 mg, 1.86 mmol) N,N-diisopropylcarbodiimide. After shaking for two hours, the resin was washed three times with methylene chloride and dried under vacuum. Amino acid analysis showed the leucine content to be 0.40 meq/g and the phenylalanine content to be 0.40 meq/g.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04764595uspto-grants-1988_08