Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Tributyltin azide | HCID 4984872 | — |
| Reactant | Tert-butyl (3-[[3-(3-cyanopropoxy)-5-(3-methoxypropyl)benzyl](cyclopropyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate | HCID 86635940 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | 1,4-Dichlorobenzene | HCID 4685 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178494885 | HCID 178494885 | — |
Reaction Steps
To a solution of tert-butyl (3-[[3-(3-cyanopropoxy)-5-(3-methoxypropyl)benzyl](cyclopropyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate from Example 74 in dichlorobenzene (0.08 M) was added azidotributyltin (2 eq.). The resulting mixture was heated to 150° C. for 22 h. The reaction was quenched with glacial acetic acid (6 eq.) and directly loaded onto a silica gel column packed with 85:15 (v/v) CH2Cl2: 2.0 M NH3 in MeOH. Elution with the same solvent system afforded the title compound as a yellow oil. MS (ESI+): 725.4.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08063105B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-5b13d84fd9094fc1806b3c6d0092a85a |
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| Source note | uspto-grants-2011_11 |
|---|