HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → (S)-2-(4'-Ethoxycarbonyl-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl)-azetidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | (2S)-1-((tert-butoxy)carbonyl)azetidine-2-carboxylic acid | HCID 2734495 | — |
| Reactant | 5'-Amino-2'-trifluoromethoxy-biphenyl-4-carboxylic acid | HCID 67372930 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (S)-2-(4'-Ethoxycarbonyl-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl)-azetidine-1-carboxylic acid tert-butyl ester | HCID 67371803 | 78.7% |
Reaction Steps
A mixture of 5′-amino-2′-trifluoromethoxy-biphenyl-4-carboxylic acid (150 mg), (S)-azetidine-1,2-dicarboxylic acid 1-tert-butyl ester (93 mg), HBTU (262 mg) and N-methyl morpholine (0.14 ml) in dry DMF (3 ml) was stirred at room temp for 18 h. The mixture was then partitioned between water and DCM. The dried organic layer was evaporated and the residue purified on silica gel. Elution with ethyl acetate:petrol 1:1 gave a pale orange oil (185 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08008303B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-65f520f383b24dc4a74c1939a07159ab |
| Source note | uspto-grants-2011_08 |