HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → 4-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxymethyl]-1-(3-trifluoromethyl-benzyl)-pyrrolidine-2-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | 4-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxymethyl]-1-(3-trifluoromethyl-benzyl)-pyrrolidine-2-carboxylic acid methyl ester | HCID 57988786 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxymethyl]-1-(3-trifluoromethyl-benzyl)-pyrrolidine-2-carboxylic acid | HCID 44236449 | — |
Reaction Steps
A mixture of solution of 4-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxymethyl]-1-(3-trifluoromethyl-benzyl)-pyrrolidine-2-carboxylic acid methyl ester (25 mg, 0.039 mmol) in THF (3 ml) and MeOH (1 ml) was added aq. solution of LiOH (3 mg, 0.079 mmol) in H2O (1 ml) at 0° C. and it was stirred for 2 hrs. Reaction mixture was concentrated, residue was diluted with water and acidified with aq. HCl. The aqueous layer was extracted with ethyl acetate and washed with brine. The ethyl acetate layer was concentrated and purified by column chromatography to offer 4-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxymethyl]-1-(3-trifluoromethyl-benzyl)-pyrrolidine-2-carboxylic acid as viscous oil (18 mg, 75%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08252797B2 |
| Source dataset | uspto-grants-2012_08 |
| ORD ID | ord-5b874389b46e498ca0ef6ccf2351a4f3 |
| Source note | uspto-grants-2012_08 |