Methanol → HCID 10918020, compound

HRID 1768495Notes

Reaction equation

HRID 1768495 reaction equation
[K+].[Br-].[CH3:3][C:4]1[S:8][CH:7]=[C:6](/[CH:9]=[C:10](/[C@H:12]2[O:29][C:27](=[O:28])[CH2:26][C@H:25]([OH:30])[C@@H:24]([CH3:31])[C:22](=[O:23])[C@H:21]([CH3:32])[C@@H:20]([OH:33])[C@@H:19]([CH3:34])[CH2:18][CH2:17][CH2:16][C:15](C)=[CH:14][CH2:13]2)\C)[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=CC2)\C)N=1.[CH3:69][OH:70]>>[CH3:3][C:4]1[S:8][CH:7]=[C:6](/[CH:9]=[C:10](/[C@H:12]2[O:29][C:27](=[O:28])[CH2:26][C@H:25]([OH:30])[C:24]([CH3:31])([CH3:36])[C:22](=[O:23])[C@H:21]([CH3:32])[C@@H:20]([OH:33])[C@@H:19]([CH3:34])[CH2:18][CH2:17][CH2:16][CH:15]=[CH:14][CH2:13]2)\[CH2:69][OH:70])[N:5]=1

Participants

5

Reactant 4

HCID 887Methanol2×HCID 253877Potassium BromideHCID 9805055HCID 9805055, compoundHCID 9955962HCID 9955962, compound

Product 1

HCID 10918020HCID 10918020, compound

Procedure

colorless amorphous solid; [α]22D −93.4 (c 1.0, MeOH); UV (MeOH) λmax nm (ε) 209 (15200), 254 (15700); IR (KBr)) νmax 3416, 2966, 2932, 1736, 1689, 1463, 1249, 1011 cm−1; 1H NMR (CDCl3, 400 MHz) δ 7.06 (1H, s, H-19), 6.65 (1H, bs, H-17), 6.56 (1H, dd, J=10.6, 4.4 Hz, 27-OH), 5.55 (1H, d, J=6.2 Hz, 3-OH),5.52 (1H, dd, J=11.6, 2.0 Hz, H-15), 5.44 (1H, dddd, J=11.2, 10.7, 3.1, 1.7 Hz, H-12), 5.35 (1H, dddd, J=11.0, 10.7, 3.9, 1.7 Hz, H-13),4.47 (11-1, ddd, J=12.5, 4.4, 1.3 Hz, H-27a), 4.35 (1H, ddd, J=11.7, 6.2, 2.6 Hz, H-3), 4.20 (1H, ddd, J=12.5, 10.6, 0.9 Hz, H-27b), 3.63 (1H, ddd, J=4.6, 1.8, 0.9 Hz, H-7), 3.24 (1H, d, J=1.8 Hz, 7-OH), 3.13 (1H, dq, J=0.9, 6.8 Hz, H-6), 2.80 (1H, ddd, J=14.8, 11.6, 11.0 Hz, H-14a), 2.71 (3H, s, H-21), 2.40 (1H, dd, J=14.4, 11.7 Hz, H-2a), 2.24 (1H, m, HI1a), 2.06 (1H, dd, J=14.4, 2.6 Hz, H-2b), 2.01 (1H, ddd; J=14.8, 3.9, 2.0 Hz, H-14b), 2.00 (1H, m, H-11b), 1.77 (1H, m, H-8),1.69 (1H, m, H-10a), 1.35 (1H, m, H-9a), 1.35 (3H, s, H23), 1.19 (1H, m, H-10b), 1.19 (3H, d, J=6.8 Hz, H-24), 1.18 (1H, m, H-9b), 1.01 (3H, d, J=7.1 Hz, H-25),0.98 (3H, H-22); 13C NMR, see Table 1; EIMS m/z 493 [M]+ (17), 306′(64), 184 (50), 171 (30), 167 (38), 166 (100), 138 (12); HREIMS m/z 493.2502 (calcd. for C26H39NO6S, 493.2498).

Sources & evidence

ORD record
ord-fb740140a68249d99890d005e3f36f6a
Source dataset
uspto-grants-2007_06
Patent number
US07235669B2

Reaction notes

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