Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Aminoacetonitrile sulfate (1:1) | HCID 196971 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 11603467 | HCID 11603467 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 23159907 | HCID 23159907 | 65.3% |
Reaction Steps
A solution of 3-(4-{[3-(1-benzothiophen-3-yl)benzyl]oxy}phenyl)propanoic acid (0.20 g, 0.51 mmol), aminoacetonitrile sulfate (65 mg, 0.62 mmol), triethylamine (0.17 mL, 1.22 mmol), 1-hydroxybenzotriazole (91 mg, 0.67 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.13 g, 0.68 mmol) in N,N-dimethylformamide (15 mL) was stirred at room temperature for 18 hr. The reaction solution was diluted with ethyl acetate, and the mixture was washed successively with aqueous citric acid solution, aqueous sodium bicarbonate and aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained pale-yellow oil was crystallized from diethyl ether to give the title compound (142 mg, yield 33%) as colorless needle crystals. MS: m/z 427 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07517910B2 |
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| Source dataset | uspto-grants-2009_04 |
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| ORD ID | ord-3320faf5d3824fcabf90bbf1a2904db2 |
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| Source note | uspto-grants-2009_04 |
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