HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dicyclohexylcarbodiimide → 3-(4-Hydroxy-phenyl)-2-(2-{2-[3-(4-hydroxy-phenyl)-propionyloxy]-acetoxy}-acetylamino)-propionic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 3-(4-Hydroxy-phenyl)-propionic acid carboxymethyl ester | HCID 58427508 | — |
| Reactant | 2-(2-Hydroxy-acetylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester | HCID 58895805 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-(4-Hydroxy-phenyl)-2-(2-{2-[3-(4-hydroxy-phenyl)-propionyloxy]-acetoxy}-acetylamino)-propionic acid methyl ester | HCID 58427512 | — |
Reaction Steps
A solution of 3-(4-hydroxy-phenyl)-propionic acid carboxymethyl ester 5 (10 grams, 44.64 mmol) and 2-(2-hydroxy-acetylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester 3 (11.3 grams, 44.66 mmol) in anhydrous dichloro methane (100 mL) under a nitrogen atmosphere at 0° C. is added dropwise to a solution of 1,3-dicyclohexyl carbodiimide (23 grams, 111.47 mmol) in dichloro methane (60 mL). The resulting solids are filtered off. The organic phase is washed with 5% sodium bicarbonate (2×25 mL) and water (2×25 mL), dried over sodium sulphate, and distilled to give crude 8, which can be purified in an appropriate solvent.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07935843B2 |
| Source dataset | uspto-grants-2011_05 |
| ORD ID | ord-0d1b5501128846deb68271661ce61039 |
| Source note | uspto-grants-2011_05 |