HCID 136124671, compound → HCID 136124682, compound
Reaction equation
[CH3:1][S:2]([O:5][C@H:6]([C:8]1[NH:9][C:10](=[O:23])[C:11]2[CH:16]=[N:15][N:14]([CH:17]3[CH2:22][CH2:21]OC[CH2:18]3)[C:12]=2[N:13]=1)[CH3:7])(=[O:4])=[O:3].O[C@H](C1NC(=O)C2C=NN(C3CCOCC3)C=2N=1)C>>[CH3:1][S:2]([O:5][C@H:6]([C:8]1[NH:9][C:10](=[O:23])[C:11]2[CH:16]=[N:15][N:14]([CH:17]3[CH2:22][CH2:21][CH2:18]3)[C:12]=2[N:13]=1)[CH3:7])(=[O:3])=[O:4]Participants
3
Procedure
Compound C18 was prepared according to the general procedure for the synthesis of C5 in Example 1, except that C17 was used in place of C4, and the chromatographic purification was carried out with 0.5% to 1% MeOH in chloroform, rather than 0% to 5% MeOH in dichloromethane, to provide C18 as a solid. Yield: 6.0 g, 19.2 mmol, 79%. LCMS m/z 311.4 (M−1). 1H NMR (400 MHz, CDCl3) 1.85 (d, J=6.6 Hz, 3H), 1.93 (m, 2H), 2.46 (m, 2H), 2.78 (m, 2H), 3.23 (s, 3H), 5.29 (m, 1H), 5.69 (q, J=6.6 Hz, 1H), 8.08 (s, 1H), 11.65 (br s, 1H). 13C NMR (100 MHz, CDCl3) δ 14.93, 20.39, 29.84, 38.75, 51.07, 74.91, 104.98, 134.71, 151.07, 155.61, 159.27.
Workup
- customCompound C18 was prepared
- customthe chromatographic purification