Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanolamine | HCID 700 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | HCID 59593534 | HCID 59593534 | — |
| Solvent | Formic Acid | HCID 284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 59593538 | HCID 59593538 | 70.1% |
Reaction Steps
To a solution of 3-{2,6-dimethyl-4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propyl]-phenyl}-propionic acid (10 mg, 22 μmol) in DMF (0.5 mL), TBTU (8 mg, 24 μmol) and DIPEA (10 mg, 72.6 μmol) is added. The mixture is stirred at rt for 5 min before ethanolamine (7 mg, 110 μmol) is added. Stirring is continued for 16 h at rt. The mixture is diluted with acetonitril (0.5 mL) and formic acid (25 μL) and separated by prep. HPLC (Waters SymmetryC18 19×50 mm 5 μm, 80% to 0% water (0.5% HCOOH) in acetonitrile) to give 3-{2,6-dimethyl-4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propyl]-phenyl}-N-(2-hydroxy-ethyl)-propionamide (7 mg) as a colourless resin; LC-MS: tR=1.03 min, [M+1]+=454.35.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07846964B2 |
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| Source dataset | uspto-grants-2010_12 |
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| ORD ID | ord-27a1ad7c29494bfd846cc81e345a32ff |
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| Source note | uspto-grants-2010_12 |
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