Potassium Bromide → HCID 9912250, compound

HRID 1768489Notes

Reaction equation

HRID 1768489 reaction equation
[K+].[Br-].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)CCC[C@H]3O[C@H]3C2)N=1.[CH3:36][C:37]1[S:41][CH:40]=[C:39](/[CH:42]=[C:43](/[C@H:46]2[O:64][C:62](=[O:63])[CH2:61][C@H:60]([OH:65])[C:59](C)([CH3:66])[C:57](=[O:58])[C@H:56]([CH3:68])[C@@H:55]([OH:69])[C@@H:54]([CH3:70])[CH2:53][CH2:52][CH2:51][C@H:49]3O[C@H:48]3[CH2:47]2)\[CH2:44]O)[N:38]=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>[CH3:36][C:37]1[S:41][CH:40]=[C:39](/[CH:42]=[C:43](/[C@H:46]2[O:64][C:62](=[O:63])[CH2:61][C@H:60]([OH:65])[C@H:59]([CH3:66])[C:57](=[O:58])[C@H:56]([CH3:68])[C@@H:55]([OH:69])[C@@H:54]([CH3:70])[CH2:53][CH2:52][CH2:51][CH:49]=[CH:48][CH2:47]2)\[CH3:44])[N:38]=1

Participants

6

Reactant 4

HCID 253877Potassium BromideHCID 9805055HCID 9805055, compoundHCID 9913011HCID 9913011, compound2×HCID 11092425HCID 11092425, compound

Product 1

HCID 9912250HCID 9912250, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

colorless amorphous solid; [α]22D −11.6 (c 10.0, MeOH); UV (MeOH) λmax nm (ε) 212 (15500), 249 (12100); IR (KBr) νmax 3428, 2962, 2929, 2877, 2859, 1734, 1705, 1460, 1251, 9S2 cm−1; 1H NM (CDCl3, 300 MHz) δ 6.99 (1H, s, H-19), 6.66 (1H, bs, H-17),5.55 (1H, ddd, J=10.4, 9.2, 6.1 Hz, H-12), 5.38 (1H, ddd, J=10.4, 9.3, 6.2 147, H-13),5.22 (1H, dd, J=8.8, 2.8 Hz, H-15), 4.42 (1H, dddd, J=9.4, 5.6, 4.2, 4.1 Hz, H-3),3.93 (1H, d, J=5.6 Hz, 3-OH), 3.86 (1H, m, H-7), 3.15 (1H, bs, 7-OH), 3.12 (1H, dq, J=4.2, 7.0 Hz, H-4), 3.00 (1H, dq, J=6.9, 7.0 Hz, H-6), 2.70 (3H, s, H-21), 2.62 (1H, dddd, J=15.1, 9.3, 8.8, 0.8 Hz, H-14a), 2.58 (1H, dd, J=15.4, 9.4 Hz, H-2a), 2.38 (1H, dd, J=15.4, 4.1 Hz, H-2b), 2.31 (1H, ddd, 0.1=15.1, 6.2, 2.8 Hz, H-14b), 2.08 (3H, d, J=1.3 Hz, H-27), 2.15 (1H, m, H-11a), 2.04 (1H, m, H-11b), 1.71 (1H, m, H-8), 1.59 (1H, m, H-10a), 1.43 (1H, m, H-9a), 1.31 (114, m, H-9b), 1.26 (3H, d, J=7.0 Hz, H-24), 1.15 (3H, d, J=7.0 Hz, H-23), 1.11 (1H, m, H-10b), 1.00 (3H, d, J=6.9 Hz, H-25); 13C NMR, see Table 1; EIMS m/z 463 [M]+ (7), 324 (7), 306 (8), 290 (17), 168 (100), 164 (14), 139 (27); HREIMS m/z 463.2392 (calcd. for C25H37NO5S, 463.2392).

Sources & evidence

ORD record
ord-a67de678f109429eb1c5cf73a1c86500
Source dataset
uspto-grants-2007_06
Patent number
US07235669B2

Reaction notes

Loading…