Reacción #334096

ord-839e1ab7a8194256b1fb8d7c2497aa41

Ecuación de reacción

CCOC(C)=O
ethyl acetate
CC(C)(C)OC(=O)N[C@@H](CCC(N)=O)C(=O)Oc1ccc([N+](=O)[O-])cc1
Boc-Gln-ONp
Oc1cccc2[nH]nnc12
hydroxy benzotriazole
CN(C)C=O
DMF
CCN1CCOCC1
N-ethylmorpholine
→
COC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)OC(C)(C)C
product
Rendimiento 82.0%
COC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)OC(C)(C)C
Boc-Gln-Gln-Gly-OMe
Rendimiento 82.0%

Reactantes

CCOC(C)=O
ethyl acetate
CC(C)(C)OC(=O)N[C@@H](CCC(N)=O)C(=O)Oc1ccc([N+](=O)[O-])cc1
Boc-Gln-ONp
Oc1cccc2[nH]nnc12
hydroxy benzotriazole
CN(C)C=O
DMF
CCN1CCOCC1
N-ethylmorpholine

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturacooled on an ice bath
  2. 2
    workup.ADDITIONadded
  3. 3
    Otrountil a pH of 7 is obtained
  4. 4
    Otroof reaction at ambient temperature
  5. 5
    Otroa precipitate is obtained which
  6. 6
    Lavadowashed with AcOEt
  7. 7
    Otrodried in vacuo

Procedimiento

A solution of the residue obtained in the preceding step (theoretically 175.9 mM) in 500 ml of DMF, cooled on an ice bath, has 77.6 g of Boc-Gln-ONp (211.1 mM), 26.4 g of hydroxy benzotriazole (211.1 mM) and N-ethylmorpholine added thereto until a pH of 7 is obtained. After 20 hrs. of reaction at ambient temperature, the solution sets en masse. By addition of ethyl acetate, a precipitate is obtained which is drained, washed with AcOEt and dried in vacuo. 64.27 g of product are obtained, viz. a yield of 82%. Monitored by NMR and TLC.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04704450uspto-grants-1987_11