C(N(CC)CC)C.[C:8]1(=[O:14])[O:13][C:11](=[O:12])[CH2:10][CH2:9]1.[N+:15]([C:18]1[CH:29]=[C:28]2[C:21]([NH:22][CH:23]=[C:24]2[CH2:25][CH2:26][NH2:27])=[CH:20][CH:19]=1)([O-])=O>CN(C1C=CN=CC=1)C.ClCCl>[CH3:8][O:13][C:11]([NH:15][C:18]1[CH:29]=[C:28]2[C:21](=[CH:20][CH:19]=1)[NH:22][CH:23]=[C:24]2[CH2:25][CH2:26][NH:27][C:11](=[O:12])[CH2:10][CH2:9][C:8]([OH:13])=[O:14])=[O:12]Triethylamine (12 mmol), DMAP (0.6 mmol), and succinic anhydride (9 mmol) are added to a solution of 5-nitrotryptamine (6 mmol) in dichloromethane (25 mL). The mixture is stirred 4 h, the solvent removed in vacuo, and the residue chromatographed on silica gel using 10% methanol-chloroform with 1% acetic acid as eluent. The product is then hydrogenated and transformed to the carbamic acid methyl ester as in the previous examples. Purified product is obtained by reverse-phase HPLC as above.
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