HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 4-[2-Cyclohexyl-2-(2-methylamino-propionylamino)-acetyl]-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | (1-{1-Cyclohexyl-2-[4-methanesulfonyl-6-(1,2,3,4-tetrahydro-naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester | HCID 67281619 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-[2-Cyclohexyl-2-(2-methylamino-propionylamino)-acetyl]-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide | HCID 67280655 | — |
Reaction Steps
A solution of 22 (222 mg, 0.3 mmol) in DCM (10 mL) was treated with TFA (3 mL) at ambient temperature. After 1.5 h, the solution was concentrated, diluted with EtOAc, washed with saturated NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated. The resulting residue was diluted with ACN/H2O containing 0.1% HOAc and purified by reverse-phase HPLC (2″ Dynamax® C18, 10-100% ACN/H2O containing 0.1% HOAc). The product-containing fractions were frozen and lyophilized to afford 23 as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08481495B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-32a88e702bad4b658f25e44d7572820d |
| Source note | uspto-grants-2013_07 |