Peptide oostatic hormone → 1,3,5-Trimethoxy-2,4,6-trinitrobenzene
Reaction equation
[CH3:1][C@H](NC([C@H]1N(C([C@@H](NC([C@@H](N)CC2C=CC(O)=CC=2)=O)CC(O)=O)=O)CCC1)=O)C(N1[C@H](C(N2[C@H](C(N3[C@H](C(N4[C@H](C(N5[C@H](C(N6[C@H](C(O)=O)CCC6)=O)CCC5)=O)CCC4)=O)CCC3)=O)CCC2)=O)CCC1)=O.COC1C([N+]([O-])=O)=C(O)C([N+]([O-])=O)=C(O)C=1[N+]([O-])=O.[CH3:95][O:96][C:97]1[C:105]([N+:106]([O-:108])=[O:107])=[C:104]([O:109][CH3:110])[C:103]([N+:111]([O-:113])=[O:112])=[C:102]([OH:114])[C:98]=1[N+:99]([O-:101])=[O:100]>>[CH3:95][O:96][C:97]1[C:105]([N+:106]([O-:108])=[O:107])=[C:104]([O:109][CH3:110])[C:103]([N+:111]([O-:113])=[O:112])=[C:102]([O:114][CH3:1])[C:98]=1[N+:99]([O-:101])=[O:100]Participants
Procedure
Alkoxylating the nitrated alkoxy derivatives forms 1,3,5-trialkoxy-2,4,6-trinitrobenzene, which remains dissolved in the organic solvent to form a 1,3,5-trialkoxy-2,4,6-trinitrobenzene/organic solvent solution. Additional organic solvent may, optionally, be added to maintain an initial volume of the organic solvent in the reaction vessel such that the 1,3,5-trialkoxy-2,4,6-trinitrobenzene remains in solution. For example, the additional organic solvent may be added to the reaction vessel to maintain a volume of from about 10 mL to about 50 mL. In one embodiment, TMOF is used as the alkoxylating agent and is reacted with the 5-methoxystyphnic acid or 3,5-dimethoxypicric acid, producing 1,3,5-trimethoxy-2,4,6-trinitrobenzene. While the example described herein utilizes TMOF as the alkoxylating agent, triethyl orthoformate or tripropyl orthoformate may be used to form 1,3,5-triethoxy-2,4,6-trinitrobenzene or 1,3,5-tripropoxy-2,4,6-trinitrobenzene, respectively.
Workup
- additionAdditional organic solvent may, optionally, be added
- temperatureto maintain a volume of from about 10 mL to about 50 mL
Sources & evidence
- ORD record
- ord-15d527ac3d51431382b3790729396a27
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07910776B2
Reaction notes
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