Potassium Bromide → HCID 9804980, compound

HRID 1768487Notes

Reaction equation

HRID 1768487 reaction equation
[K+].[Br-].[CH3:3][C:4]1[O:8][CH:7]=[C:6](/[CH:9]=[C:10](/[C@H:12]2[O:30][C:28](=[O:29])[CH2:27][C@H:26]([OH:31])[C:25]([CH3:33])([CH3:32])[C:23](=[O:24])[C@H:22]([CH3:34])[C@@H:21]([OH:35])[C@@H:20]([CH3:36])[CH2:19][CH2:18][CH2:17][C@@:15]3([CH3:37])O[C@H:14]3[CH2:13]2)\[CH3:11])[N:5]=1.CCC1SC=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.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)CCC[C@H]3O[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>CO>[CH3:3][C:4]1[O:8][CH:7]=[C:6](/[CH:9]=[C:10](/[C@H:12]2[O:30][C:28](=[O:29])[CH2:27][C@H:26]([OH:31])[C:25]([CH3:33])([CH3:32])[C:23](=[O:24])[C@H:22]([CH3:34])[C@@H:21]([OH:35])[C@@H:20]([CH3:36])[CH2:19][CH2:18][CH2:17][C:15]([CH3:37])=[CH:14][CH2:13]2)\[CH3:11])[N:5]=1

Participants

7

Reactant 5

HCID 253877Potassium BromideHCID 9847893HCID 9847893, compoundHCID 9847978HCID 9847978, compoundHCID 9870258HCID 9870258, compoundHCID 10791734HCID 10791734, compound

Product 1

HCID 9804980HCID 9804980, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

colorless amorphous solid; [α]22D −44.4 (c 0.25, MeOH); UV (MeOH) λmax nm (ε) 203 (14500), 236 (12200); IR (KBr) νmax 3436, 2967, 2935, 2880, 1734, 1690, 1586, 1251, 1007 cm−1; 1H NMR (CDCl3, 400 MHz) δ 7.46 (1H, s, H-19), 6.30 (1H, bs, H-17), 5.23 (1H, dd, J=9.8, 2.1 Hz, H-15), 5.12 (1H, dd, J=10.1, 5.3 Hz, H-13), 4.20 (1H, ddd, J=10.8, 5.7, 2.9 Hz, H-3), 3.71 (1H, ddd, J=3.8, 2.6, 2.6 Hz, H-7),3.14 (1H, dq, J=2.6, 6.9 Hz, H-6), 2.93 (d, J=5.7 Hz, 3-OH), 2.90 (1H, bd, J=2.6 Hz, 7-OH), 2.62 (1H, ddd, J=15.1, 9.8, 9.8 Hz, H-14a), 2.46 (1H, dd, J=15.1, 10.8 Hz, H-2a), 2.43 (3H, s, H-21), 2.32 (1H, dd, J=15.1, 2.9 Hz, H-2b), 2.29 (1H, m, H-11a), 2.19 (1H, bd, J=15.1 Hz, H-14b), 1.97 (3H, d, J=1.3 Hz, H-27), 1.87 (1H, m, H-11b), 1.73 (1H, m, H-8), 1.67 (1H, m, H-10a), 1.65 (3H, bs, H-26), 1.32 (3H, s, H-23), 1.26 (2H, m, H-9), 1.24 (1H, m, H-10b), 1.18 (3H, d, J=6.9 Hz, H-24), 1.07 (3H, s, H-22), 1.00 (3H, d, J=7.0 Hz, H-25); 13C NMR (CDCl3, 100 MHz) δ 220.6 (s, C-5), 170.3 (s, C-1), 161.0 (s, C-20), 138.6 (s, C-12), 138.4 (s, C-16), 137.5 (s, C-18), 135.6 (d, C-19), 120.8 (d, C-13), 115.8 (d, C-17), 78.9 (d, C-15), 74.3 (d, C-7), 72.7 (d, C-3), 53.3 (s, C-4), 42.0 (d, C-6), 39.6 (t, C-2), 38.6 (d, C-8), 32.4 (t, C-14), 31.9 (t, C-9), 31.6 (t, C-11), 25.6 (t, C-10), 23.0 (q, C-26), 22.8 (q, C-23), 18.8 (q, C-22), 16.1 (q, C-27), 15.9 (q, C-25), 13.8 (q, C-21), 13.6 (q, C-24); EIMS m/z 475 [M]+ (11), 288 (9), 287 (5), 188(7), 171 (32), 152 (100), 111 (10); HREIMS m/z 475.2913 (calcd. for C27H41NO6, 475.2934).

Sources & evidence

ORD record
ord-438dd035d577472dbb061c97518717ac
Source dataset
uspto-grants-2007_06
Patent number
US07235669B2

Reaction notes

Loading…