Reacción #4517

ord-9c82aae6872744659c78caf24f2a0ad6

Ecuación de reacción

O
water
COC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)OC(C)(C)C
L-Ala-D-Glu(OH)OBzl
COC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)OC(C)(C)C
Boc-L-Ala-D-Glu(OH)OMe
C[Si](C)(C)C(C(N)=O)[Si](C)(C)C
bis(trimethylsilyl)acetamide
CCCCCCCCCCCCCCCCCC(=O)Cl
stearoyl chloride
→
CCCCCCCCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)O)C(=O)OCc1ccccc1
stearoyl-L-Ala-D-Glu(OH)OBzl
Rendimiento 196.4%

Reactantes

O
water
COC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)OC(C)(C)C
L-Ala-D-Glu(OH)OBzl
COC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)OC(C)(C)C
Boc-L-Ala-D-Glu(OH)OMe
C[Si](C)(C)C(C(N)=O)[Si](C)(C)C
bis(trimethylsilyl)acetamide
CCCCCCCCCCCCCCCCCC(=O)Cl
stearoyl chloride

Reactivos

Ninguno

Disolventes

ClCCl
methylene chloride

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.WAITleft for an hour
  2. 2
    OtroEvaporation of the solvent
  3. 3
    Otrogave an oily residual which
  4. 4
    Otroto give white solides
  5. 5
    FiltraciónThe solides were collected by filtration
  6. 6
    Lavadowashed with water
  7. 7
    Secadodried over magnesium sulfate

Procedimiento

L-Ala-D-Glu(OH)OBzl (1) (942 mg) was suspended in methylene chloride (40 ml), and bis(trimethylsilyl)acetamide (1.20 g) was added to the suspension under stirring. The resulting solution was treated with stearoyl chloride (900 mg) at ambient temperature and left for an hour. Evaporation of the solvent gave an oily residual which was treated with water to give white solides. The solides were collected by filtration, washed with water and dried over magnesium sulfate to give stearoyl-L-Ala-D-Glu(OH)OBzl (2) (1.60 g).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04725582uspto-grants-1988_02