Reaktion #86639

Reaktionsgleichung

EtOAc DCM

Benzyl chloroformate

Amine

(7S,10S,13S)-13-Amino-10-isobutyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo[13.2.2]nonadeca-1-(18),15(19),16-triene-7-carboxylic acid methyl ester hydrogen chloride salt

DIPEA

→

(7S,10S,13S)-13-Benzyloxycarbonylamino-10-isobutyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo-[13.2.2]nonadeca-1(18),15(19),16-triene-7-carboxylic acid methyl ester

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONadded
2. 2
   Sonstigebefore being partitioned between chloroform and 1M hydrochloric acid
3. 3
   ExtraktionThe aqueous phase was extracted three more times with chloroform
4. 4
   Trocknenthe combined organic extracts were dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigePurification
8. 8
   Wascheneluting with a gradient of 15% EtOAc/DCM to 50% EtOAc/DCM
9. 9
   Sonstigeto yield an off-white solid, 2.10 g, 43%

Vorschrift

Amine 6 (4.00 g, 8.78 mmol) was dissolved in anhydrous DMF (30 mL). Benzyl chloroformate (1.88 mL, 13.2 mmol) and DIPEA (6.11 mL, 35.1 mmol) were, added and the reaction mixture was stirred at rt for 18 h before being partitioned between chloroform and 1M hydrochloric acid. The aqueous phase was extracted three more times with chloroform and the combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification was achieved using flash chromatography, eluting with a gradient of 15% EtOAc/DCM to 50% EtOAc/DCM to yield an off-white solid, 2.10 g, 43%. R1=0.43 (30% EtOAc/DCM).

Quelle