Tert-butyl 5-(5-(5-(3-chloro-4-propoxy phenyl)-1,2,4-oxadiazol-3-yl)benzofuran-2-yl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate → 2-Amino-2-(5-octylbenzo[b]thiophen-2-yl)propane-1,3-diol

HRID 717729Notes

Reaction equation

HRID 717729 reaction equation
ClC1C=C(C2ON=C(C3C=CC4OC(C5(NC(=O)OC(C)(C)C)COC(C)(C)OC5)=CC=4C=3)N=2)C=CC=1OCCC.CC1(C)[O:48][CH2:47][C:46]([NH:66]C(=O)OC(C)(C)C)([C:49]2[S:53][C:52]3[CH:54]=[CH:55][C:56]([CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])=[CH:57][C:51]=3[CH:50]=2)[CH2:45][O:44]1>>[NH2:66][C:46]([C:49]1[S:53][C:52]2[CH:54]=[CH:55][C:56]([CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])=[CH:57][C:51]=2[CH:50]=1)([CH2:47][OH:48])[CH2:45][OH:44]

Participants

3

Reactant 2

HCID 66614932Tert-butyl 5-(5-(5-(3-chloro-4-propoxy phenyl)-1,2,4-oxadiazol-3-yl)benzofuran-2-yl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateHCID 86660636tert-Butyl 2,2-dimethyl-5-(5-octylbenzo[b]thiophen-2-yl)-1,3-dioxan-5-ylcarbamate

Product 1

HCID 462001512-Amino-2-(5-octylbenzo[b]thiophen-2-yl)propane-1,3-diolYield 38%

Procedure

When tert-butyl 5-(5-(5-(3-chloro-4-propoxyphenyl)-1,2,4-oxadiazol-3-yl)benzofuran-2-yl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate was replaced with the product of Step C the similar procedure as described in Example 36, Step E gave the title compound (0.008 g, 38%) as light yellow solid. 1H NMR (CD3OD) 7.74 (d, 1H, J=8.28 Hz); 7.6 (s, 1H); 7.4 (s, 1H); 7.2 (dd, 2H, J=8.34, 1.59 Hz); 4.0 (d, 2H, J=11.46 Hz); 3.94 (d, 2H, J=11.46 Hz); 2.7 (t, 2H, J=7.53 Hz); 1.64 (b, 2H); 1.34-1.26 (b, 10H); 0.85 (t, 3H, J=4.8 Hz).

Sources & evidence

ORD record
ord-bf59d8578ed34ad28a81b59f6cfb25e4
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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