HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → {2-[4-(2-Amino-3,3-dimethyl-butyryl)-3-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-carbamic acid benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | {1-[4-(2-Benzyloxycarbonylamino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid tert-butyl ester | HCID 67282206 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | {2-[4-(2-Amino-3,3-dimethyl-butyryl)-3-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-carbamic acid benzyl ester | HCID 67281524 | 92.4% |
Reaction Steps
A solution of 57 (570 mg) in DCM (10 mL) was treated with TFA (3 mL) at ambient temperature. After 2 h, the solution was concentrated, diluted with EtOAc, and washed with saturated NaHCO3. The aqueous phase was back extracted with DCM and the combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 58 (450 mg) which was used without further purification. Mass spectrum, m/z [586.4] (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08481495B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-8a14be68781b431096f6b0c4b001e8f6 |
| Source note | uspto-grants-2013_07 |