Potassium Bromide → HCID 9890595, compound

HRID 1768488Notes

Reaction equation

HRID 1768488 reaction equation
[K+].[Br-].[CH3:3][C:4]1[S:8][CH:7]=[C:6](/[CH:9]=[C:10](/[C@H:12]2[O:30][C:28](=[O:29])[CH2:27][C@H:26]([OH:31])[C@@H:25]([CH3:32])[C:23](=[O:24])[C@H:22]([CH3:33])[C@@H:21]([OH:34])[C@@H:20]([CH3:35])[CH2:19][CH2:18][CH2:17][C@H:15]3O[C@H:14]3[CH2:13]2)\[CH3:11])[N:5]=1.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)\CO)N=1.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>CO>[CH3:3][C:4]1[S:8][CH:7]=[C:6](/[CH:9]=[C:10](/[C@H:12]2[O:30][C:28](=[O:29])[CH2:27][C@H:26]([OH:31])[C@@H:25]([CH3:32])[C:23](=[O:24])[C@H:22]([CH3:33])[C@@H:21]([OH:34])[C@@H:20]([CH3:35])[CH2:19][CH2:18][CH2:17][CH:15]=[CH:14][CH2:13]2)\[CH3:11])[N:5]=1

Participants

6

Reactant 4

HCID 253877Potassium BromideHCID 9847978HCID 9847978, compoundHCID 9913011HCID 9913011, compoundHCID 11092425HCID 11092425, compound2×

Product 1

HCID 9890595HCID 9890595, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

colorless amorphous solid; [α]22D −114.0 (c 10.0, MeOH); UV (MeOH) λmax nm (ε) 211 (16500), 248 (12500); IR (KBr) νmax 3440, 2933, 2877, 2858, 1730, 1708, 1457, 1244, 981 cm−1; 1H NMR (CDCl3, 300 MHz) δ 6.96 (1H, s, H-19), 6.56 (1H, bs, H-17), 5.47 (1H, dd, J=9.2, 3.0 Hz, H-15), 5.43 (1H, m, H-12), 5.40 (1H, m, H-13), 4.40 (1H, ddd, J=6.2, 6.1, 6.1 Hz, H-3), 3.69 (1H, dd, J=5.7, 3.6 Hz, H-7), 3.01 (1H, dq, J=5.7, 6.9 Hz, H-6), 3.01 (1H, bs, 3-OH), 2.84 (1H, dq, J=5.2, 7.0 Hz, H-4), 2.68 (3H, s, H-21), 2.66 (1H, ddd, 1=16.4, 9.2, 7.3 Hz, H-14a), 2.64 (1H, dd, J=15.9, 7.1 Hz, H-2a), 2.54 (1H, dd, J=15.9, 6.1 Hz, H-2b), 2.38 (1H, bd, J=16.4 Hz, H-14b), 2.35 (1H, bs, 7-OH), 2.07 (3H, bs, H-27), 2.03 (2H, m, H-11), 1.62 (1H, m, H-10a), 1.53 (1H, m, H-8), 1.35 (1H, m, H-9a), 1.22 (1H, M, H-9b), 1.19 (3H, d, J=6.9 Hz, H-24),1.14 (3H, d, J=6.9 Hz, H-23), 1.10 (1H, m, H-10b), 0.95 (3H, d, J=6.9 Hz, H-25); 13C NMR, see Table 1; EIMS m/z 463 [M]+ (5), 324 (8), 290 (8), 204 (7), 168 (100), 164 (15), 139 (36); HREIMS m/z 463.2381 (calcd. for C23H37NO5S, 463.2392).

Sources & evidence

ORD record
ord-f2da9b8c01a74ac391c16b0278136c1d
Source dataset
uspto-grants-2007_06
Patent number
US07235669B2

Reaction notes

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