Reacción #86646

Ecuación de reacción

EtOAc DCM

Benzyl chloroformate

DIPEA

Amine

(8S,11S,14S)-14-Amino-11-isobutyl-10,13-dioxo-2-oxa-9,12-diaza-bicyclo[14.2.2]icosa-1(19),16(20),17-triene-8-carboxylic acid methyl ester hydrochloride

→

(8S,11S,14S)-14-Benzyloxycarbonylamino-11-isobutyl-10,13-dioxo-2-oxa-9,12-diaza-bicyclo[14.2.2]icosa-1(19),16(20),17-triene-8-carboxylic acid methyl ester

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrobefore being partitioned between EtOAc and 1M hydrochloric acid
2. 2
   ExtracciónThe aqueous phase was extracted twice more with EtOAc
3. 3
   Secadothe combined organic extracts were dried (MgSO4)
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe crude material was purified by flash chromatography on silica using a gradient of EtOAc/DCM
7. 7
   Otroto yield an off-white solid, 0.460 g, 69%

Procedimiento

Amine 25 (0.550 g, 1.17 mmol) was dissolved in anhydrous DMF (20 mL). Benzyl chloroformate (0.250 mL, 1.76 mmol) and DIPEA (0.815 mL, 4.68 mmol) were added and the reaction mixture was stirred at rt for 18 h before being partitioned between EtOAc and 1M hydrochloric acid. The aqueous phase was extracted twice more with EtOAc and the combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica using a gradient of EtOAc/DCM to yield an off-white solid, 0.460 g, 69%. Rf=0.32 (30% EtOAc/DCM). m.p. 91-93° C.

Fuente