Dicyclohexylcarbodiimide → 2-[5-(4-Isobutylphenyl)-1,2,4-oxadiazol-3-yl]-4,5,6,7-tetrahydro-1-benzothiophen-4-ol

HRID 2247671Notes

Reaction equation

HRID 2247671 reaction equation
[Si]([O:8][CH:9]1[C:14]2[CH:15]=[C:16]([C:18](=[N:20][OH:21])[NH2:19])[S:17][C:13]=2[CH2:12][CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[CH2:22]([C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=O)=[CH:28][CH:27]=1)[CH:23]([CH3:25])[CH3:24].C1(N=C=NC2CCCCC2)CCCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH2:22]([C:26]1[CH:27]=[CH:28][C:29]([C:30]2[O:21][N:20]=[C:18]([C:16]3[S:17][C:13]4[CH2:12][CH2:11][CH2:10][CH:9]([OH:8])[C:14]=4[CH:15]=3)[N:19]=2)=[CH:33][CH:34]=1)[CH:23]([CH3:25])[CH3:24]

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 381114-Isobutylbenzoic acidHCID 2724141Tetrabutylammonium FluorideHCID 866202174-{[t-butyl(dimethyl)silyl]oxy}-N'-hydroxy-4,5,6,7-tetrahydro-1-benzothiophene-2-carboximidamide

Product 1

HCID 685210992-[5-(4-Isobutylphenyl)-1,2,4-oxadiazol-3-yl]-4,5,6,7-tetrahydro-1-benzothiophen-4-ol

Procedure

The crude product of the title compound was synthesized by conducting the similar reaction to that mentioned in Example 2 (2c) using 4-{[t-butyl(dimethyl)silyl]oxy}-N′-hydroxy-4,5,6,7-tetrahydro-1-benzothiophene-2-carboximidamide (0.15 g, 0.50 mmol) that was obtained in Example 8 (8e), 4-isobutylbenzoic acid (89 mg, 0.50 mmol), N,N′-dicyclohexylcarbodiimide (0.11 g, 0.55 mmol), and a 1.0 M solution of tetrabutylammonium fluoride (0.75 ml, 0.75 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:1) as the eluent to afford the title compound (92 mg) in a yield of 52% as a colourless oily product.

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-04e8ca431e3f446ca751fb97cb955557
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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