Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | HCID 68540058 | HCID 68540058 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 68540187 | HCID 68540187 | 32% |
Reaction Steps
t-Butyl 2-(2-benzylamino-1-(4-methoxybenzyl)ethylamino)-3-methylbutyrate (0.64 g; 1.5 mmol) was dissolved in toluene (40 ml). Triethylamine (457 μL; 3.3 mmol) and triphosgene (0.49 g; 1.65 mmol) were added. The reaction mixture was stirred at RT for 4.5 h. It was then washed with water (1×), saturated NaHCO3 solution (1×) and again with water (1×). The organic phase was dried over Na2SO4 and concentrated in a rotary evaporator. The crude product was chromatographed on an SiO2 cartridge (EtOAc/n-heptane 1:3). t-Butyl 2-(3-benzyl-5-(4-methoxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyrate (0.22 g, 0.48 mmol) was obtained as a yellow oil. MS: 453.20 (M+H); Rt: 1.94 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07652143B2 |
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| Source dataset | uspto-grants-2010_01 |
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| ORD ID | ord-1295227030eb4524868a1b81b2a23e10 |
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| Source note | uspto-grants-2010_01 |
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