Probucol → 2,6-Di-tert-butyl-4-{1-[3,5-di-tert-butyl-4-(2-ethoxy-5(R)-hydroxymethyl-[1,3]dioxolan-4(R)-ylmethoxy)-phenylsulfanyl]-1-methyl-ethylsulfanyl}-phenol

HRID 916989

Reaktionsgleichung

Reaktionsgleichung von HRID 916989
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:16][C:17]([S:20][C:21]2[CH:26]=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:24]([OH:31])=[C:23]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:22]=2)([CH3:19])[CH3:18])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].[CH2:36]([O:38][CH:39]1[O:43][C@H:42]([CH2:44]O)[C@@H:41]([CH2:46][OH:47])[O:40]1)[CH3:37]>>[C:12]([C:9]1[CH:8]=[C:7]([S:16][C:17]([S:20][C:21]2[CH:22]=[C:23]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:24]([O:31][CH2:44][C@@H:42]3[C@@H:41]([CH2:46][OH:47])[O:40][CH:39]([O:38][CH2:36][CH3:37])[O:43]3)=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:26]=2)([CH3:18])[CH3:19])[CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:13])([CH3:14])[CH3:15]

Komponenten

3

Edukt 2

HCID 4912ProbucolHCID 585933702-ethoxy-1,3-dioxolane-4(R),5(R)-dimethanol

Produkt 1

HCID 585933712,6-Di-tert-butyl-4-{1-[3,5-di-tert-butyl-4-(2-ethoxy-5(R)-hydroxymethyl-[1,3]dioxolan-4(R)-ylmethoxy)-phenylsulfanyl]-1-methyl-ethylsulfanyl}-phenol

Versuchsvorschrift

The title compound was prepared using the same procedure as described in Ex-1A starting from probucol and 2-ethoxy-1,3-dioxolane-4(R),5(R)-dimethanol as a white solid (10.3 g, 35%), mp 60–62° C. 1H-NMR (300 MHz, CDCl3) δ 7.56 (s, 2H), 7.44 (s, 2H), 5.89 (s, 1H), 5.36 (s, 1H), 4.75–4.78 (m, 1H), 4.19–4.24 (m, 2H), 3.92–3.99 (m, 2H), 3.84 (dd, 1H, J=10.0, 4.2 Hz), 3.60–3.74 (m, 2H), 2.79 (dd, 1H, J=9.1, 3.3 Hz). 1.43–1.45 (m, 42H), 1.28 (t, 3H, J=7.2 Hz). HRMS (ESI) calcd for C38H60O6S2 (M+Na), 699.3729; found, 699.3756. Anal. calcd. for C38H60O6S2: C, 67.42, H, 8.93, S, 9.47; found: C, 67.04, H, 9.00, S, 8.86.

Quellen und Nachweise

ORD-Eintrag
ord-0e0adb5440154fd8b14d68ffa61b6abe
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271274B2

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