Potassium Bromide → HCID 10939534, compound

HRID 1168650Notes

Reaction equation

HRID 1168650 reaction equation
[K+].[Br-].[CH3:3][C:4]1[S: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@H:25]([CH3:32])[C:23](=[O:24])[C@H:22]([CH3:33])[C@@H:21]([OH:34])[C@@H:20]([CH3:35])[CH2:19][CH2:18][CH2:17][C@H:15]3O[C@H:14]3[CH2:13]2)\[CH3:11])[N:5]=1.CC1SC=C(/C=C(/[C@H]2OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)CCCCC=CC2)\C)N=1.CC1SC=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(C)=CCCC(C)=CC2)\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)CCCC(C)=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(C)=CCCC=CC2)\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)CCCC(C)=CC2)\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)CCCC=CC2)\C)N=1>CO>[CH3:3][C:4]1[S: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@H:25]([CH3:32])[C:23](=[O:24])[C@H:22]([CH3:33])[C@@H:21]([OH:34])[C@@H:20]([CH3:35])[CH2:19][CH2:18][CH2:17][CH:15]=[CH:14][CH2:13]2)\[CH3:11])[N:5]=1

Participants

11

Reactant 9

HCID 253877Potassium BromideHCID 9805055HCID 9805055, compoundHCID 9847903HCID 9847903, compound2×HCID 9912250HCID 9912250, compoundHCID 9912251HCID 9912251, compoundHCID 9934122HCID 9934122, compoundHCID 9956788HCID 9956788, compoundHCID 10885254HCID 10885254, compoundHCID 11134719HCID 11134719, compound

Product 1

HCID 10939534HCID 10939534, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

colorless amorphous solid; [α]D22−84 (c 0.2, MeOH); UV (MeOH) λmax nm (ε) 211 (17400), 248 (12900); IR (KBr) νmax 3433, 2961, 2933, 2879, 1730, 1708, 1457, 1251, 975 cm−1; 1H NMR (CDCl3, 600 MHz) δ 7.00 (1H, s, H-19), 6.64 (1H, bs, H-17), 5.45 (1H, ddd, J=15.2, 6.5, 6.5 Hz, H-12), 5.42 (1H, dd, J=6.4, 3.7 Hz, H-15), 5.35 (1H, dt, J=15.2, 7.1 Hz, H-13), 4.42 (1H, m, H-3), 3.58 (1H, ddd, J=8.1, 7.9, 2.8 Hz, H-7), 3.24 (1H, m, H-6), 3.14 (1H, dq, J=4.0, 6.9 Hz, H-6), 2.92 (1H, d, J=7.9 Hz, 7-OH), 2.71 (3H, s, H-21), 2.71 (2H, m, H-2), 2.53 (2H, m, H-14), 2.17 (1H, d, J=2.17 Hz, 3-OH), 2.11 (1H, m, H-11a), 2.06 (3H, bs, H-27), 1.93 (1H, m, H-11b), 1.68 (1H, m, H-9a), 1.65 (1H, m, H-10a), 1.33 (1H, m, H-8), 1.26 (3H, d, J=6.8 Hz, H-24), 1.16 (1H, m, H-10b), 1.12 (3H, d, J=6.9 Hz, H-22), 1.07 (1H, m, H-9b), 1.00 (3H, d, J=6.8 Hz, H-25); 13C NMR, see Table 1; EIMS m/z 463 [M]+ (6), 290 (21), 289 (20), 204 (23), 194 (19), 190 (22), 168 (100), 164 (48), 157 (14), 152 (19), 151 (17), 139 (15), 111 (18), HREIMS m/z 463.2371 (calcd. for C25H37NO5S, 463.2392).

Sources & evidence

ORD record
ord-056356ed76e145dbb4de4a7504749f11
Source dataset
uspto-grants-2003_09
Patent number
US06624310B1

Reaction notes

Loading…