Reaktion #587571

ord-d5d0f92c60d54f68941f38a7c0509b97

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)OCO2
3,4-methylenedioxybenzoyl chloride
→
CC(C)(C)OC(=O)NC1CCCCCC=CC2CC2(C(=O)NS(=O)(=O)C2CC2)NC(=O)C2CC(OC(=O)c3ccc4c(c3)OCO4)CN2C1=O
18-(3,4-methylenedioxybenzoyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]-nonadec-7-ene
Ausbeute 35.1%

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)OCO2
3,4-methylenedioxybenzoyl chloride

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

Prepared by way of method I 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 3,4-methylenedioxybenzoyl chloride (65 μL, 0.35 mmol). The final trituration (diethyl ether/hexane) and filtration gave 44 mg (35%) of 18-(3,4-methylenedioxybenzoyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]-nonadec-7-ene as a white powder: 98.6% pure (HPLC), MS m/z 717 (M+H)+, HRMS: calcd. 717.2806 and found 717.2789 (M+H)+, mp 153-155° C.

Quelle

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