Potassium Bromide → HCID 11134719, compound

HRID 1168646Notes

Reaction equation

HRID 1168646 reaction equation
[K+].[Br-].CC1[S:8]C=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]1O[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:57]([CH3:65])([CH3:64])[C:55](=[O:56])[C@H:54]([CH3:66])[C@@H:53]([OH:67])[C@@H:52]([CH3:68])[CH2:51][CH2:50][CH2:49][C:48]([CH3:69])=[CH:47][CH2:46]2)\[CH3:44])[N:38]=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.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>CO>[CH3:36][C:37]1[S:8][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:57]([CH3:65])([CH3:64])[C:55](=[O:56])[C@H:54]([CH3:66])[C@@H:53]([OH:67])[C:52]([CH3:68])=[CH:51][CH2:50][CH2:49][C:48]([CH3:69])=[CH:47][CH2:46]2)\[CH3:44])[N:38]=1

Participants

7

Reactant 5

HCID 253877Potassium BromideHCID 9804980HCID 9804980, compoundHCID 9847893HCID 9847893, compound2×HCID 9912251HCID 9912251, compoundHCID 9913011HCID 9913011, compound

Product 1

HCID 11134719HCID 11134719, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

colorless amorphous solid; [α]D22−150 (c 0.2, MeOH); UV (MeOH) λmax nm (ε) 205 (23300), 248 (13600); IR (KBr) νmax 3439, 2967, 2927, 1736, 1690, 1451, 1254, 1181, 987 cm−1; 1H NMR (CDCl3, 400 MHz) δ; 6.94 (1H, s, H-19), 6.51 (1H, bs, H-17), 5.34 (1H, bs, H-9), 5.29 (1H, dd, J=8.0, 2.4 Hz, H-15), 5.16 (1H, dd, J=8.2, 6.2 Hz, H-13), 4.30 (1H, bd, J=4.9 Hz, H-7), 4.19 (1H, ddd, J=10.8, 7.6, 3.0 Hz, H-3), 3.68 (1H, d, J=7.6 Hz, 3-OH), 3.17 (1H, dq, J=4.9, 7.0 Hz, H-6), 2.69 (3H, s, H-21), 2.65 (1H, d, J=2.1 Hz, 7-OH), 2.56 (1H, ddd, J=16.2, 8.2, 8.0 Hz, H-14a), 2.40 (1H, dd, J=15.0, 3.0 Hz, H-2a), 2.39 (1H, bd, J=16.2 Hz, H-14b), 2.34 (1H, dd, J=15.0, 10.8 Hz, H-2b), 2.25 (2H, m, H-10a and H-11a), 2.20 (1H, m, H-10b), 2.17 (1H, m, H-11b), 2.05 (3H, d, J=1.0 Hz, H-27), 1.69 (3H, bs, H-25), 1.68 (3H, bs, H-26), 1.29 (3H, s, H-23), 1.23 (3H, d, J=7.0 Hz, H-24), 1.16 (3H, s, H-22); 13C NMR, see Table 1; EIMS m/z 489 [M]+ (4), 406 (4), 338 (7), 302 (13), 218 (35), 171 (10), 168 (100), 153 (20), 125 (10); HREIMS m/z 489.2536 (calcd. for C27H39NO5S, 489.2549).

Sources & evidence

ORD record
ord-70b700773e51451ca0ca23ccc4ee1733
Source dataset
uspto-grants-2003_09
Patent number
US06624310B1

Reaction notes

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