Tetrahydrofuran → {4-Ethyl-5-[5-(4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-2-thienyl}methanol
Reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Si]([O:46][CH2:47][C:48]1[S:52][C:51]([C:53](=[N:55]O)[NH2:54])=[C:50]([CH2:57][CH3:58])[CH:49]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>>[CH2:57]([C:50]1[CH:49]=[C:48]([CH2:47][OH:46])[S:52][C:51]=1[C:53]1[N:55]=[C:12]([C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:16][CH:15]=2)[O:14][N:54]=1)[CH3:58]Participants
Reactant 6
HCID 8028Tetrahydrofuran
HCID 751824-Phenoxybenzoic acid
HCID 757711-Hydroxybenzotriazole
HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride
HCID 2724141Tetrabutylammonium Fluoride
HCID 725011755-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-ethyl-N'-hydroxythiophene-2-carboximidamideProduct 1
Procedure
The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 12 (12a) using 4-phenoxybenzoic acid (0.12 g, 0.53 mmol), 1-hydroxybenzotriazole (74 mg, 0.55 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.11 g, 0.55 mmol), 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-3-ethyl-N′-hydroxythiophene-2-carboximidamide (0.16 g, 0.50 mmol) that was obtained in Example 10 (10d), and 1.0 M solution of tetrabutylammoniumfluoride in tetrahydrofuran (1.0 mL, 1.0 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 (1:3) as the eluent to afford the title compound (0.17 g) in a yield of 89% as a pale yellowish crystalline solid.
Workup
- customthe reaction similar to
Sources & evidence
- ORD record
- ord-c2984eac6d71445f911b47f1c0e69ece
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687491B2
Reaction notes
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