Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylamine | HCID 6341 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | Isobutyl chloroformate | HCID 62365 | — |
| Reactant | 2-(((Tert-butoxy)carbonyl)amino)-2-(4-chlorophenyl)acetic acid | HCID 2756781 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66871077 | HCID 66871077 | 43% |
Reaction Steps
To 1.1 g (3.85 mM) of [(tert-butoxycarbonyl)amino](4-chlorophenyl)acetic acid in 10 ml of tetrahydrofurane were added, under stirring at −25° C., 0.5 ml (4.6 mM) of 4-methyl morpholine and 0.52 ml (4.0 mM) of isobutyl chloroformate. After 10 mn were then added, at −25° C. under stirring, 1.9 ml (3.85 mM) of ethylamine 2M in tetrahydrofurane. The reaction mixture was stirred at −25° C. for 1 h, and at room temperature for 16 h. The reaction mixture was filtered and the filtrate was concentrated under vacuum to give an oil, which was further purified by silica gel column chromatography, using dichloromethane/cyclohexane (75/25) as eluant, to give 520 mg of tert-butyl 1-(4-chlorophenyl)-2-(ethylamino)-2-oxoethylcarbamate as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09233937B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-3f6dbcc915974f35bdee4cf63a2a0070 |
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| Source note | uspto-grants-2016_01 |
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