Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzoyl chloride | HCID 7412 | — |
| Reactant | 4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid methyl ester | HCID 67409757 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67408824 | HCID 67408824 | 94.4% |
Reaction Steps
A solution containing amine 50 (258 mg, 0.5 mmol) in DCM (8 mL) was cooled to 0° C. TEA (73 mg, 0.72 mmol) was added followed by benzoyl chloride (85 mg, 0.61 mmol) and the reaction mixture was warmed to ambient temperature. After 20 min, the reaction mixture was diluted with DCM and the resulting organic solution was washed successively with 1M HCl and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by flash silica gel chromatography (hexanes/EtOAc, 1:1) to afford 278 mg (94%) of 55 as an off-white-colored foam. Mass spectrum, m/z [589.4] (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08399683B2 |
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| Source dataset | uspto-grants-2013_03 |
|---|
| ORD ID | ord-9836e17187a741b0a20ca9fd2c9d3414 |
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| Source note | uspto-grants-2013_03 |
|---|
