Pyromellitic dianhydride → HCID 69721180, compound

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[O:7][C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[CH2:11][NH:12][C@@H:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1.[CH:26]1[C:31]2[C:32]([O:34][C:35](=[O:36])[C:30]=2[CH:29]=[C:28]2[C:37]([O:39][C:40](=[O:41])[C:27]=12)=[O:38])=[O:33].C(N(C(C)C)CC)(C)C.C([O-])([O-])=[O:52].[Na+].[Na+]>>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[O:7][C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[CH2:11][N:12]([C@@H:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1)[C:32]([C:31]1[CH:26]=[C:27]([C:40]([OH:39])=[O:41])[C:28]([C:37]([OH:52])=[O:38])=[CH:29][C:30]=1[C:35]([OH:34])=[O:36])=[O:33]

Participants

Reactant 4

HCID 6966Pyromellitic dianhydride

HCID 10340Sodium Carbonate

HCID 81531Diisopropylethylamine

HCID 69720977HCID 69720977, compound

Product 1

HCID 69721180HCID 69721180, compound

Procedure

The product from Example 107A, 1,2,4,5-benzenetetracarboxylic dianhydride (0.125 g, 0.57 mmol) and diisopropylethyl amine (0.4 mL, 2.3 mmol) were processed as described in Example 1B. The reaction mixture was treated with saturated Na2CO3 solution (30 mL) and stirred vigorously at room temperature for 1 hour. The layers were separated and the aqueous layer was acidified with 1N HCl. The acidified aqueous layer was evaporated under reduced pressure to afford a solid. Soxhlet extraction (ethanol) of the crude solid, followed by RP-HPLC, provided the title compound (4 mg).