Potassium Bromide → HCID 9826235, compound

HRID 1168647Notes

Reaction equation

HRID 1168647 reaction equation
[K+].[Br-].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)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.C[CH2:70][C:71]1[S:75][CH:74]=[C:73](/[CH:76]=[C:77](/[C@H:79]2[O:97][C:95](=[O:96])[CH2:94][C@H:93]([OH:98])[C:92]([CH3:100])([CH3:99])[C:90](=[O:91])[C@H:89]([CH3:101])[C@@H:88]([OH:102])[C@@H:87]([CH3:103])[CH2:86][CH2:85][CH2:84][C@H:82]3O[C@H:81]3[CH2:80]2)\[CH3:78])[N:72]=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.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>[CH3:70][C:71]1[S:75][CH:74]=[C:73](/[CH:76]=[C:77](/[C@H:79]2[O:97][C:95](=[O:96])[CH2:94][C@H:93]([OH:98])[C:92]([CH3:100])([CH3:99])[C:90](=[O:91])[C@H:89]([CH3:101])[C@@H:88]([OH:102])[C@@H:87]([CH3:103])[CH2:86][CH:85]=[CH:84][CH:82]=[CH:81][CH2:80]2)\[CH3:78])[N:72]=1

Participants

8

Reactant 6

HCID 253877Potassium BromideHCID 9804980HCID 9804980, compoundHCID 9805055HCID 9805055, compoundHCID 9890595HCID 9890595, compoundHCID 9912250HCID 9912250, compoundHCID 10791734HCID 10791734, compound

Product 1

HCID 9826235HCID 9826235, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

colorless amorphous solid; [α]D22−205.2 (c 1.0, MeOH); UV (MeOH) λmax nm (ε) 218 (24600), 237 (28800); IR (KBr) νmax 3435, 2967, 2927, 2882, 1732, 1688, 1465, 1258, 988 cm−1; 1H NMR (CDCl3, 300 MHz) δ 6.97 (1H, s, H-19), 6.58 (1H, bs, H-17), 6.43 (1H, dd, 15.5, 10.8 Hz, H-11), 6.11 (1H, dd, J=10.8, 10.6 Hz, H-12), 5.75 (1H, ddd, J=15.5, 8.3, 5.6 Hz, H-10), 5.34 (1H, m, H-13), 5.34 (1H, dd, J=9.7, 2.4 Hz, H-15), 4.16 (1H, ddd, J=9.2, 4.9, 4.3 Hz, H-3), 3.74 (1H, ddd, J=2.2, 2.1, 1.7 Hz, H-7), 3.24 (1H, dq, J=2.1, 6.9 Hz, H-6), 3.06 (1H, d, J=2.2 Hz, 7-OH), 2.93 (1H, d, J=4.9 Hz, 3-OH), 2.78 (1H, dddd, J=14.1, 9.9 9.7, 0.7, H-14a), 2.71 (3H, s, H-21), 2.48 (1H, m, H-9a), 2.47 (1H, dd, J=15.5, 9.2 Hz, H-2a), 2.40 (1H, dd, J=15.5, 4.3 Hz, H-2b), 2.38 (1H, bdd, J=14.1, 7.8 Hz, H-14b), 2.11 (3)H, d, J=1.3 Hz, H-27), 1.96 (1H, m, H-8), 1.33 (3H, s, H-23), 1.11 (3H, d, J=6.9 Hz, H-24), 1.06 (3H, H-22), 1.05 (3H, d, J=6.8 Hz, H-25); 13C NMR, see Table 1; EIMS m/z 475 [M]+ (13), 387 (2), 316 (4), 288 (15), 230 (16), 204 (9), 171 (18), 168 (100), 164 (14), 151 (17); HREIMS m/z 475.2361 (calcd. for C26H37NO5S, 475.2392).

Sources & evidence

ORD record
ord-c8a056e7061442198e9ff04a9dff1f4e
Source dataset
uspto-grants-2003_09
Patent number
US06624310B1

Reaction notes

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