Reacción #479210

ord-0602082d8bd340fe8e1ebfba263caed2

Ecuación de reacción

CCN(CC)CC
Triethylamine
C(=NC1CCCCC1)=NC1CCCCC1
1,3-dicyclohexylcarbodiimide
CN[C@H](CC(C)C)C(=O)N[C@H]1C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H]2C(=O)N[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)O)c4cc(O)cc(O)c4-c4cc3ccc4O)[C@H](O)c3ccc(c(Cl)c3)Oc3cc2cc(c3O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@H]2C[C@](C)(N)[C@H](O)[C@H](C)O2)Oc2ccc(cc2Cl)[C@H]1O.Cl
vancomycin hydrochloride
ON1CSc2ccccc21
N-hydroxybenzothiazole
→
CN[C@H](CC(C)C)C(=O)N[C@H]1C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H]2C(=O)N[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)O)c4cc(O)cc(O)c4-c4cc3ccc4O)[C@H](O)c3ccc(c(Cl)c3)Oc3cc2cc(c3O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@H]2C[C@](C)(N)[C@H](O)[C@H](C)O2)Oc2ccc(cc2Cl)[C@H]1O
vancomycin

Reactantes

CCN(CC)CC
Triethylamine
C(=NC1CCCCC1)=NC1CCCCC1
1,3-dicyclohexylcarbodiimide
—
amine
CN[C@H](CC(C)C)C(=O)N[C@H]1C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H]2C(=O)N[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)O)c4cc(O)cc(O)c4-c4cc3ccc4O)[C@H](O)c3ccc(c(Cl)c3)Oc3cc2cc(c3O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@H]2C[C@](C)(N)[C@H](O)[C@H](C)O2)Oc2ccc(cc2Cl)[C@H]1O.Cl
vancomycin hydrochloride
ON1CSc2ccccc21
N-hydroxybenzothiazole

Reactivos

Ninguno

Disolventes

CN(C)C=O
DMF

Condiciones de reacción

Temperatura
50°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe solvent was evaporated to dryness
  2. 2
    LavadoThe residue was eluted on a silica gel column firstly using ethyl acetate:methanol:dichloromethane:ammonium hydroxide (6:6:2:1.2 by volume)
  3. 3
    workup.ADDITIONThe ammonium-methanol fractions containing vancomycin bidentate
  4. 4
    Otrothe solvent was evaporated

Procedimiento

Triethylamine (2 mL) was added to a DMF solution (30 mL) containing vancomycin hydrochloride (1 g), biotinlyated amine (biotin-hexanediamine-aminocaproic acid, 0.4 g), and N-hydroxybenzothiazole (200 mg). After addition of 1,3-dicyclohexylcarbodiimide (1.48 g), the mixture was heated at 50° C. for 10 h and then left at ambient temperature for overnight. The solvent was evaporated to dryness. The residue was eluted on a silica gel column firstly using ethyl acetate:methanol:dichloromethane:ammonium hydroxide (6:6:2:1.2 by volume), and then 5-7% by volume of ammonium hydroxide in methanol. The ammonium-methanol fractions containing vancomycin bidentate was pooled, and the solvent was evaporated to give the solid vancomycin bidentate (yield: 0.16 g).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06800608B2uspto-grants-2004_10