Reaction equation
[OH:1][CH:2]1[CH2:20][CH:19]2[N:4]([C:5](=[O:39])[CH:6]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][CH:14]3[C:16]([C:22]([NH:24][S:25]([CH:28]4[CH2:30][CH2:29]4)(=[O:27])=[O:26])=[O:23])([NH:17][C:18]2=[O:21])[CH2:15]3)[CH2:3]1.[N:40]1[C:49]2[C:44](=[CH:45][C:46]([C:50](Cl)=[O:51])=[CH:47][CH:48]=2)[N:43]=[CH:42][CH:41]=1>>[N:40]1[C:49]2[C:44](=[CH:45][C:46]([C:50]([O:1][CH:2]3[CH2:20][CH:19]4[N:4]([C:5](=[O:39])[CH:6]([NH:31][C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][CH:14]5[C:16]([C:22]([NH:24][S:25]([CH:28]6[CH2:30][CH2:29]6)(=[O:27])=[O:26])=[O:23])([NH:17][C:18]4=[O:21])[CH2:15]5)[CH2:3]3)=[O:51])=[CH:47][CH:48]=2)[N:43]=[CH:42][CH:41]=1Participants
3
Procedure
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, 0.176 mmol) and 6-quinoxalinecarbonyl chloride (68 mg, 0.35 mmol). The final trituration (diethyl ether/hexane) and filtration gave 48 mg (38%) of 18-(6-quinoxalinecarbonyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]-nonadec-7-ene as a white powder: 98.5% pure (HPLC), MS m/z 723 (M−H)−, HRMS: calcd. 725.2969 and found 725.2947 (M+H)+, mp 158-160° C.
Workup
- customPrepared by way of method I
- filtrationThe final trituration (diethyl ether/hexane) and filtration
Sources & evidence
- ORD record
- ord-12bd5710626f4ed0a793b938c46576f0
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772183B2
Linked notes
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