2-Iodo-4-octylbenzenethiol → 2-Amino-2-(5-octylbenzo[b]thiophen-2-yl)propane-1,3-diol

HRID 2046134Notes

Reaction equation

HRID 2046134 reaction equation
CC1(C)[O:7][CH2:6][C:5]([NH:25]C(=O)OC(C)(C)C)([C:8]2[S:12][C:11]3[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:16][C:10]=3[CH:9]=2)[CH2:4][O:3]1.IC1C=C(CCCCCCCC)C=CC=1S.ClC1C=C(C2ON=C(C3C=CC(O)=C(I)C=3)N=2)C=CC=1OCCC>>[NH2:25][C:5]([C:8]1[S:12][C:11]2[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:16][C:10]=2[CH:9]=1)([CH2:6][OH:7])[CH2:4][OH:3]

Participants

4

Reactant 3

HCID 666151462-Iodo-4-octylbenzenethiolHCID 86660636tert-Butyl 2,2-dimethyl-5-(5-octylbenzo[b]thiophen-2-yl)-1,3-dioxan-5-ylcarbamateHCID 1363599364-(5-(3-Chloro-4-propoxyphenyl)-1,2,4-oxadiazol-3-yl)-2-iodophenol

Product 1

HCID 462001512-Amino-2-(5-octylbenzo[b]thiophen-2-yl)propane-1,3-diolYield 24%

Procedure

tert-Butyl 2,2-dimethyl-5-(5-octylbenzo[b]thiophen-2-yl)-1,3-dioxan-5-ylcarbamate When with the product of Step B was substituted for 4-(5-(3-chloro-4-propoxyphenyl)-1,2,4-oxadiazol-3-yl)-2-iodophenol in Example 36, Step D, the similar procedure afforded the title compound in 24% yield, as white solid. 1H NMR (CDCl3) 7.65 (d, 1H, J=8.16 Hz); 7.47 (s, 1H); 7.1 (d, 1H, J=6.18 Hz); 7.1 (s, 1H); 5.44 (b, 1H); 4.16 (b, 4H); 2.66 (t, 2H, J=7.5 Hz); 1.6-1.1 (m, 27H); 0.86 (t, 3H, J=6.18 Hz).

Sources & evidence

ORD record
ord-5d457afd40134559a66fed6f4153eb9e
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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