HuagongsheHuagongshe Chemistry Print Report · For research reference only
Propionyl chloride → N-Isopropyl-4-methoxy-3-(3-methoxy-propoxy)-N-{(3R,4S)4-[(phenethyl-propionyl-amino)-methyl]-pyrrolidin-3-ylmethyl}-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Propionyl chloride | HCID 62324 | — |
| Reactant | 2-nitro-N-phenethylbenzenesulfonamide | HCID 779555 | — |
| Reactant | 4-Methoxy-3-(3-methoxypropoxy)benzoic acid | HCID 19039502 | — |
| Reactant | ((3S*,4R*)-1-Benzyl-4-hydroxymethyl-pyrrolidin-3-ylmethyl)-isopropyl-carbamic acid tert-butyl ester | HCID 68616191 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Product | N-Isopropyl-4-methoxy-3-(3-methoxy-propoxy)-N-{(3R,4S)4-[(phenethyl-propionyl-amino)-methyl]-pyrrolidin-3-ylmethyl}-benzamide | HCID 11851830 | — |
Reaction Steps
The title compound is prepared analogously as described in Example 361 using ((3S*,4R*)-1-benzyl-4-hydroxymethyl-pyrrolidin-3-ylmethyl)-isopropyl-carbamic acid tert-butyl ester and 2-nitro-N-phenethyl-benzenesulfonamide in step F, then propionyl chloride as the acylating agent in step H and 3-(3-methoxy-propoxy)-4-methoxy-benzoic acid as acylating agent in step J. MS (LC-MS): 554.4 [M+H]+; tR (HPLC, Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 5.26 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07807709B2 |
| Source dataset | uspto-grants-2010_10 |
| ORD ID | ord-17df73a270cb43fe80eb6b3e6a227574 |
| Source note | uspto-grants-2010_10 |