HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 4-[[(6r,7As)-2-(2-bromophenyl)-hexahydro-6-hydroxy-1-oxo-3h-pyrrolo[1,2-c]imidazol-3-ylidene]amino]-3-hydroxybenzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N'-(2-bromophenyl)carbodiimide | HCID 12043083 | — |
| Reactant | Hydroxy l-proline methyl ester hydro chloride | HCID 21063054 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 4-[[(6r,7As)-2-(2-bromophenyl)-hexahydro-6-hydroxy-1-oxo-3h-pyrrolo[1,2-c]imidazol-3-ylidene]amino]-3-hydroxybenzonitrile | HCID 9888746 | 78% |
Reaction Steps
The standard procedure was followed using N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N′-(2-bromophenyl)carbodiimide (102 mg, 0.24 mmol), diisopropylethylamine (60 μL, 0.26 mmol), hydroxy L-proline methyl ester hydro chloride (44 mg, 0.26 mmol) and TBAF (0.29 mL, 0.29 mmol) in THF (2.5 mL) and methanol (0.1 mL) to give 80 mg (78%) of 4-[[(6R,7aS)-2-(2-bromophenyl)-hexahydro-6-hydroxy-1-oxo-3H-pyrrolo[1,2-c]imidazol-3-ylidene]amino]-3-hydroxybenzonitrile as a tan powder. MS(EI) m/e 427 (100 (M+)).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06566387B1 |
| Source dataset | uspto-grants-2003_05 |
| ORD ID | ord-53f9b60870fa40c6ad66cea13b863a50 |
| Source note | uspto-grants-2003_05 |