Potassium Bromide → HCID 9912250, compound

HRID 1168643Notes

Reaction equation

HRID 1168643 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:45]2[O:62][C:60](=[O:61])[CH2:59][C@H:58]([OH:63])[C@@H:57]([CH3:64])[C:55](=[O:56])[C@H:54]([CH3:65])[C@@H:53]([OH:66])[C@@H:52]([CH3:67])[CH2:51][CH2:50][CH2:49][C:48](C)=[CH:47][CH2:46]2)\[CH3:44])[N:38]=1>CO>[CH3:36][C:37]1[S:41][CH:40]=[C:39](/[CH:42]=[C:43](/[C@H:45]2[O:62][C:60](=[O:61])[CH2:59][C@H:58]([OH:63])[C@H:57]([CH3:64])[C:55](=[O:56])[C@H:54]([CH3:65])[C@@H:53]([OH:66])[C@@H:52]([CH3:67])[CH2:51][CH2:50][CH2:49][CH:48]=[CH:47][CH2:46]2)\[CH3:44])[N:38]=1

Participants

5

Reactant 3

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

Product 1

HCID 9912250HCID 9912250, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

colorless amorphous solid; [α]D22−11.6 (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, 982 cm−1; 1H NMR (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 Hz, 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, J=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 (1H, 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-5a0dbf410d8a404e8b884a653a3c249b
Source dataset
uspto-grants-2003_09
Patent number
US06624310B1

Reaction notes

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