Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Ethyl 5-bromo-2-chlorobenzoate | HCID 144749 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | Tert-butyl 1,4-diazepane-1-carboxylate | HCID 2756058 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 68670654 | HCID 68670654 | 28.9% |
Reaction Steps
A mixture of 5-bromo-2-chloro-benzoic acid, ethyl ester (0.50 g), hexahydro-1H-1,4-diazepine-1-carboxylic acid, 1,1-dimethylethyl ester (0.46 g), cesium carbonate (0.86 g), palladium (II) acetate (8.5 mg) and (R)-BINAP (35 mg) in toluene (3 ml) was heated at 100° C. for 14 h in a pressure vessel flushed with nitrogen. The cooled reaction mixture was poured into water and extracted (3 times) with ethyl acetate. The combined organic extracts were washed with saturated sodium chloride solution and then dried over magnesium sulfate. Evaporation under reduced pressure gave an oil which was purified by chromatography over silica gel, eluting with 20% ethyl acetate in iso-hexane to yield the subtitle compound as an oil (0.21 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06492355B1 |
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| Source dataset | uspto-grants-2002_12 |
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| ORD ID | ord-89db27d8275a4d948ca2286c38e91ac9 |
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| Source note | uspto-grants-2002_12 |
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