HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-Butyl Formate → (3S*,4R*)-3-{[Cyclopropyl-(2-methoxycarbonyl-2-methyl-propoxycarbonyl)-amino]-methyl}-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-Butyl Formate | HCID 61207 | — |
| Reactant | Methyl 3-hydroxypivalate | HCID 84152 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | (3R*,4R*)-3-Cyclopropylaminomethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 68616408 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Product | (3S*,4R*)-3-{[Cyclopropyl-(2-methoxycarbonyl-2-methyl-propoxycarbonyl)-amino]-methyl}-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 68616980 | — |
Reaction Steps
The title compound is prepared analogously as described above for NVP-BGW706 from ((3R*,4R*)-3-cyclopropylaminomethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester and methyl 2,2-dimethyl-3-hydroxypropionate using bis(trichloromethyl) carbonate. MS (LC-MS): 592.1 [M+H-Boc]+; tR (HPLC, Macherey-Nagel 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): 5.92 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07807709B2 |
| Source dataset | uspto-grants-2010_10 |
| ORD ID | ord-965cfc24a3234eb79399368a17430b45 |
| Source note | uspto-grants-2010_10 |