Potassium Bromide → HCID 11102633, compound

HRID 1768497Notes

Reaction equation

HRID 1768497 reaction equation
[K+].[Br-].[CH3:3][C:4]1O[CH:7]=[C:6](/[CH:9]=[C:10](/[C@H:12]2[O:29][C:27](=[O:28])[CH2:26][C@H:25]([OH:30])[C:24](C)([CH3:31])[C:22](=[O:23])[C@H:21]([CH3:33])[C@@H:20]([OH:34])[C@@H:19]([CH3:35])[CH2:18][CH2:17][CH2:16][C:15](C)=[CH:14][CH2:13]2)\[CH3:11])[N:5]=1.CC1OC=C(/C=C(/[C@H]2OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCC[C@@]3(C)O[C@H]3C2)\C)N=1.CC1OC=C(/C=C(/[C@H]2OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCC[C@H]3O[C@H]3C2)\C)N=1.CC1[S:111]C=C(/C=C(/[C@H]2OC(=O)C[C@H](O)C(C)(C)C(=O)C[C@@H](O)[C@@H](C)CCCC=CC2)\C)N=1.CC1SC=C(/C=C/[C@H]2OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCCC=CC2)N=1.CC1SC=C(/C=C(/[C@H]2OC(=O)C[C@H](O)[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCCC(C)=CC2)\C)N=1>CO>[CH3:3][C:4]1[S:111][CH:7]=[C:6](/[CH:9]=[C:10](/[C@H:12]2[O:29][C:27](=[O:28])[CH2:26][C@H:25]([OH:30])[C@@H:24]([CH3:31])[C:22](=[O:23])[C@H:21]([CH3:33])[C@@H:20]([OH:34])[C@@H:19]([CH3:35])[CH2:18][CH2:17][CH2:16][CH:15]=[CH:14][CH2:13]2)\[CH3:11])[N:5]=1

Participants

9

Reactant 7

HCID 253877Potassium BromideHCID 9804980HCID 9804980, compoundHCID 9805055HCID 9805055, compoundHCID 9847893HCID 9847893, compoundHCID 9870258HCID 9870258, compoundHCID 9912251HCID 9912251, compoundHCID 10906699HCID 10906699, compound

Product 1

HCID 11102633HCID 11102633, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

colorless amorphous solid; [α]22D −3 (c 1.5, MeOH); UV (MeOH) λmax nm (ε) 211 (15800), 248 (11900); IR (KBr) νmax 3435, 2963, 2931, 2878, 1731, 1706, 1457, 1273, 979 cm−1; 1H NMR (CDCl3, 600 MHz) δ 6.99 (1H, s, H-19), 6.57 (1H, bs, H17), 5.56*(1H, ddd, J=15.1, 7.4, 7.0 Hz, H-12), 5.41 (1H, ddd, J=15.1, 7.0, 6.9 Hz, H-13), 5.41 (1H, dd, J=7.7, 2.8 Hz, H-15), 4.13 (1H, dddd, J=6.7, 6.2, 5.6, 5.1 Hz, H-3), 3.78 (1H, ddd, J=8.2, 6.5, 1.9 Hz, H-7), 3.18 (1H, d, J=5.6 Hz, 3-OH), 3.06 (1H, dq, J=8.2, 7.1 Hz, H-6),2.98 (1H, dq, J=6.2, 7.0 Hz, H-4), 2.71 (3H, s, H-21),2.64 (1H, dd, J=15.1, 6.7 Hz, H2a), 2.54 (1H, dd, J=15.1, 5.1 Hz, H-2b), 2.44 (2H, m, H-14),2.22 (1H, dddd, J=13.8, 7.0, 6.2, 2.9 Hz, H-11a), 2.10 (3H, d, J=1.1 Hz, H-27), 2.09 (˜H, d, J=6.5 Hz, 7-OH), 1.88 (1H, dddd, J=13.8, 10.9, 7.4, 2.9 Hz, H-11b), 1.65 (1H, m, H-8), 1.63 (1H, m, H-10a), 1.56 (1H, dddd, J=12.7, 12.7, 3.9, 3.9 Hz, H-9a), 1.20 (3H, d, J=7.1 Hz, H-24), 1.15 (3H, d, J=7.0 Hz, H-23),1.13 (1H, m, H-10b), 1.04 (1H, m, H-9.b), 1.01 (3H, d, J=7.0 Hz, H-25); 13C NMR, see Table 1; EIMS m/z 463 [M]+ (13), 290 (11), 190 (10), 168 (100), 164 (20), 157 (26), 139 (17); HREIMS m/z 463.2383 (calcd. for C25H37NO5S, 463.2392).

Sources & evidence

ORD record
ord-d0380cd327b243609849fe504d73452d
Source dataset
uspto-grants-2007_06
Patent number
US07235669B2

Reaction notes

Loading…