Borane → Tetramethylammonium hydroxide
Reaction equation
S1CCSCCNCCSCCSCCNC[CH2:2]1.[O:19]=[C:20]1[CH2:37][N:36]([S:38]([C:41]2[CH:47]=[CH:46][C:44]([CH3:45])=[CH:43][CH:42]=2)(=[O:40])=[O:39])[CH2:35][CH2:34][N:33]([S:48]([C:51]2[CH:57]=[CH:56][C:54]([CH3:55])=[CH:53][CH:52]=2)(=[O:50])=[O:49])[CH2:32][C:31](=O)[N:30]2[CH2:59][CH2:60][S:61][CH2:62][CH2:63][S:64][CH2:65][CH2:66][N:21]1[CH2:22][CH2:23][S:24][CH2:25][CH2:26][S:27][CH2:28][CH2:29]2.B.B#B>>[OH-:19].[CH3:29][N+:30]([CH3:59])([CH3:2])[CH3:31].[S:38]([N:36]1[CH2:35][CH2:34][N:33]([S:48]([C:51]2[CH:52]=[CH:53][C:54]([CH3:55])=[CH:56][CH:57]=2)(=[O:49])=[O:50])[CH2:32][CH2:31][N:30]2[CH2:29][CH2:28][S:27][CH2:26][CH2:25][S:24][CH2:23][CH2:22][N:21]([CH2:66][CH2:65][S:64][CH2:63][CH2:62][S:61][CH2:60][CH2:59]2)[CH2:20][CH2:37]1)([C:41]1[CH:47]=[CH:46][C:44]([CH3:45])=[CH:43][CH:42]=1)(=[O:39])=[O:40]Participants
Procedure
Treat the cyclic diamine prepared in Example 33 with N,N'-ditosylethylenediamine-N,N'-diacetyl dichloride prepared in Example 66A in the manner of Example 3 followed by treatment of the thereby formed 2,9-dioxo-4,7-ditosyl-13,16,21,24-tetrathia-1,4,7,10-tetraazabicyclo[8,8,8]hexacosane with boron hydride in the manner of Example 6 followed by hydrolysis of the diborane derivative thereby formed and thence treatment of the resulting hydrochloride salt with tetramethylammonium hydroxide to obtain 4,7-ditosyl-13,16,21,24-tetrathia-1,4,7,10-tetraazabicyclo-[8,8,8]hexacosane. Treat the foregoing 4,7-ditosylbicyclictetraazaalkane with lithium in liquid ammonia according to the procedure of Example 4 to obtain 13,16,21,24-tetrathia-1,4,7,10-tetraazabicyclo[8,8,8]hexacosane.
Workup
- customthereby formed
Sources & evidence
- ORD record
- ord-db27e3cee26f429aa91f41916398d24c
- Source dataset
- uspto-grants-1976_06
- Patent number
- US03966766
Reaction notes
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