HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 4-(2-Amino-2-cyclohexyl-acetyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester | HCID 67281489 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-(2-Amino-2-cyclohexyl-acetyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester | HCID 67281672 | 86.3% |
Reaction Steps
A solution of 16 (346 mg, 0.64 mmol) in DCM (10 mL) was treated with TFA (3 mL) at ambient temperature. After 1 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 17 (245 mg) as an orange-colored foam that was used without further purification. Mass spectrum, m/z [444.4] (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08481495B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-064124e6be2c474793d1561fa328825b |
| Source note | uspto-grants-2013_07 |