Reaktion #86646

Reaktionsgleichung

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

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle