Reaktion #587577

ord-a8c31f8b965141a397e8699f208f35ea

Reaktionsgleichung

CC(C)(C)OC(=O)NC1CCCCCC=CC2CC2(C(=O)NS(=O)(=O)C2CC2)NC(=O)C2CC(O)CN2C1=O
18-hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]-nonadec-7-ene
O=C(Cl)c1ccc2c(c1)OCCO2
2,3-dihydro-1,4-benzodioxine-6-carbonyl chloride
→
CC(C)(C)OC(=O)NC1CCCCCC=CC2CC2(C(=O)NS(=O)(=O)C2CC2)NC(=O)C2CC(OC(=O)c3ccc4c(c3)OCCO4)CN2C1=O
18-(2,3-dihydro-1,4-benzodioxine-6-carbonyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]-nonadec-7-ene
Ausbeute 39.1%

Edukte

CC(C)(C)OC(=O)NC1CCCCCC=CC2CC2(C(=O)NS(=O)(=O)C2CC2)NC(=O)C2CC(O)CN2C1=O
18-hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]-nonadec-7-ene
O=C(Cl)c1ccc2c(c1)OCCO2
2,3-dihydro-1,4-benzodioxine-6-carbonyl chloride

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePrepared by way of method II
  2. 2
    FiltrationThe final trituration (diethyl ether/hexane) and filtration

Vorschrift

Prepared by way of method II using 18-hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]-nonadec-7-ene (100 mg, 0.175 mmol) and 2,3-dihydro-1,4-benzodioxine-6-carbonyl chloride (105 mg, 0.53 mmol). The final trituration (diethyl ether/hexane) and filtration gave 50 mg (39%) of 18-(2,3-dihydro-1,4-benzodioxine-6-carbonyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]-nonadec-7-ene as a white powder: 99.5% pure (HPLC), MS m/z 729 (M−H)−, HRMS: calcd. 748.3228 and found 748.3220 (M+NH4)+, mp 199-201° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07772183B2uspto-grants-2010_08