Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | o-Chlorophenylacetic acid | HCID 17124 | — |
| Reactant | Bromine | HCID 24408 | — |
| Reactant | Phosphorus tribromide | HCID 24614 | — |
| Reactant | Pyrrolidine, 1-[(2R)-2-hydroxy-1-oxopropyl]- (9CI) | HCID 11194401 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 44544858 | HCID 44544858 | 86% |
Reaction Steps
To phosphorus tribromide (28 g, 103.4 mmol), 2-chlorophenylacetic acid (44 g, 257.9 mmol) was added. The mixture was stirred at 50° C. for 1 hour. After stirring, bromine (66 g, 413.0 mmol) was added thereto at the same temperature for reaction overnight. After the reaction, toluene (200 mL) and (2R)-1-oxo-1-pyrrolidinylpropane-2-ol (40.6 g, 283.6 mmol) were added thereto at the same temperature. Subsequently, triethylamine (34 g, 336.0 mmol) was added thereto to carry out reaction for 2 hours. After the reaction, water was added thereto. After the mixture was neutralized with a 30% sodium hydroxide aqueous solution, the organic layer was separated from the water layer and the water layer was disposed of. The obtained organic layer was washed with water, and the water layer was separated and disposed of. The organic layer was concentrated under reduced pressure to obtain 83.1 g of the target compound (221.8 mmol, 86%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08383833B2 |
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| Source dataset | uspto-grants-2013_02 |
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| ORD ID | ord-bb3f5046be184fe1897458afbad647d5 |
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| Source note | uspto-grants-2013_02 |
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