Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 5-Chloro-2-methoxybenzeneethanamine | HCID 20984849 | — |
| Reactant | 3-{2-[(2R)-2-(tert-butyldimethyl silanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid | HCID 57978309 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | Ammonia | HCID 222 | — |
| Product | 3-[2-({(2R)-2-{[tert-Butyl(dimethyl)silyl]oxy}-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)-2-methylpropyl]-N-[2-(5-chloro-2-methoxyphenyl)ethyl]benzamide | HCID 69023356 | — |
Reaction Steps
A mixture of 3-{2-[(2R)-2-(tert-butyldimethylsilanyloxy)-2-(4-hydroxy-3-hydroxy methylphenyl)ethylamino]-2-methylpropyl}benzoic acid (preparation 37) (400 mg, 0.85 mmol), O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (320 mg, 0.85 mmol), triethylamine (225 μL, 1.6 mmol) and 2-(5-chloro-2-methoxy-phenyl)-ethylamine (preparation 70), (64 mg, 0.85 mmol) in N,N-dimethylacetamide (8 mL) was stirred for 18 hours at room temperature. The solvent was removed in vacuo and the residue was partitioned between dichloromethane (4 mL) and saturated sodium hydrogen carbonate solution (1 mL). The organic solution was then dried over magnesium sulfate, concentrated in vacuo and the residue was purified using an ISCO Companion® silica cartridge, eluting with dichloromethane:methanol:0.88 ammonia, 90:10:1 to 80:20:2, to afford the title compound in 22% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07629358B2 |
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| Source dataset | uspto-grants-2009_12 |
|---|
| ORD ID | ord-d589937ccd834c09bdc44c1bcf609949 |
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| Source note | uspto-grants-2009_12 |
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