HuagongsheHuagongshe Chemistry Print Report · For research reference only
Terephthaloyl chloride → Trifluoroacetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Terephthaloyl chloride | HCID 7488 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | N-((1S,2R,3S,4R)-4-{6-(2,2-Diphenyl-ethylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate | HCID 66630460 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | Trifluoroacetic acid | HCID 6422 | — |
| Product | 4-[(R)-3-(3-{(R)-1-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-ureido)-pyrrolidine-1-carbonyl]-benzoic acid trifluoroacetate | HCID 86647552 | — |
Reaction Steps
A solution of N-((1S,2R,3S,4R)-4-{6-(2,2-diphenyl-ethylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate (step 1) (0.02 g, 29 μmol) DIPEA (0.0075 g, 58 μmol) in NMP (0.2 ml) is treated with a solution of terephthaloyl chloride (0.006 g, 14.5 μmol) in NMP (0.1 ml). After stirring at room temperature for 1 hour the reaction mixture is purified by C-18 reverse phase column chromatography eluting with acetonitrile:water:TFA (0.1%) (gradient of 0 to 100% acetonitrile) to yield the title compound. (MH+ 831.6)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08318750B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-df7787a2d24648f38946e77a62cb3204 |
| Source note | uspto-grants-2012_11 |