HuagongsheHuagongshe Chemistry Print Report · For research reference only
Indole-4-carboxylic acid → tert-butyl 1-(1H-indol-4-yl)-1-oxo-5,8,11-trioxa-2-azatetradecan-14-oate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Indole-4-carboxylic acid | HCID 595229 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | tert-Butyl 12-amino-4,7,10-trioxadodecanoate | HCID 16218573 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | tert-butyl 1-(1H-indol-4-yl)-1-oxo-5,8,11-trioxa-2-azatetradecan-14-oate | HCID 86705966 | — |
Reaction Steps
To a mixture of 1H-indole-4-carboxylic acid (322 mg, 2.00 mmol), tert-butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate (554 mg, 2.00 mmol), and diisporopylethylamine (700 μL, 4.00 mmol) in DMF (3 mL) was added HATU (950 mg, 2.50 mmol) and the solutions stirred for 16 h. The solvent was removed and the resulting residue was purified by silica gel chromatography, using a gradient of 70% to 100% EtOAc in hexanes as eluent and the solvent removed. This gave 557 mg (66%) of the product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09301951B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-ef0eeece608c435fad2fe153aadcd12f |
| Source note | uspto-grants-2016_04 |