Potassium Bromide → HCID 9934122, compound

HRID 1168644Notes

Reaction equation

HRID 1168644 reaction equation
[K+].[Br-].[CH3:3][C:4]1[S:8][CH:7]=[C:6](/[CH:9]=[CH:10]/[C@H:11]2[O:29][C:27](=[O:28])[CH2:26][C@H:25]([OH:30])[C:24]([CH3:32])([CH3:31])[C:22](=[O:23])[C@H:21]([CH3:33])[C@@H:20]([OH:34])[C@@H:19](C)[CH2:18][CH2:17][CH2:16][C@H:14]3O[C@H:13]3[CH2:12]2)[N:5]=1.[CH3:36]C1OC=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>CO>[CH3:3][C:4]1[S:8][CH:7]=[C:6](/[CH:9]=[C:10](/[C@H:11]2[O:29][C:27](=[O:28])[CH2:26][C@H:25]([OH:30])[C:24]([CH3:32])([CH3:31])[C:22](=[O:23])[C@H:21]([CH3:33])[C@@H:20]([OH:34])[CH2:19][CH2:18][CH2:17][CH2:16][CH:14]=[CH:13][CH2:12]2)\[CH3:36])[N:5]=1

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 9804980HCID 9804980, compoundHCID 9913011HCID 9913011, compound

Product 1

HCID 9934122HCID 9934122, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

colorless amorphous solid; [α]D22−75.6 (c 1.0, MeOH); UV (MeOH) λmax nm (ε) 212 (17200), 248 (12500); IR (KBr) νmax 3434, 2974, 2932, 2859, 1735, 1686, 1252, 1046 cm−1; 1H NMR (CDCl3, 300 MHz) δ 6.96 (1H, s, H-19), 6.60 (1H, bs, H-17), 5.43 (1H, m, H-12), 5.40 (1H, m, H-13), 5.26 (1H, dd, J=9.6, 2.3 Hz, H-15), 4.41 (1H, ddd, J=11.4, 5.8, 2.5 Hz, H-3), 3.78 (1H, m, H-7), 3.70 (1H, bs, 3-OH), 3.46 (1H, d, J=0.9 Hz, 7-OH), 3.01 (1H, dq, J=0.5, 7.0 Hz, H-6), 2.69 (3H, s, H-21), 2.66 (1H, ddd, J=15.3, 9.6, 8.8 Hz, H-14a), 2.47 (1H, dd, J=14.5, 11.4 Hz, H-2a), 2.29 (1H, m, H-14b), 2.25 (1H, dd, J=14.5, 2.5 Hz, H-2b), 2.24 (1H, m, H-11a), 2.07 (3H, d, J=1.4 Hz, H-27), 1.96 (1H, m, H-11b), 1.51 (2H, m, H-8), 1.44 (2H, m, H-10), 1.37 (2H, m, H-9), 1.32 (3H, s, H-23), 1.17 (3H, d, J=7.0 Hz, H-24), 1.07 (3H, s, H-22); 13C NMR see Table 1; EIMS m/z 463 [M]+ (7), 276 (15), 171 (33), 168 (100), 164 (23), 151 (22), 111 (13); HREIMS m/z 463.2373 (calcd. for C25H37NO5S, 463.2392).

Sources & evidence

ORD record
ord-612d171b5627402eaa2c80c256b6266b
Source dataset
uspto-grants-2003_09
Patent number
US06624310B1

Reaction notes

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