HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Octyne → tert-Butyl-5-((4-(N-(3-methoxyphenyl)-N-methylsulfamoyl)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Octyne | HCID 12370 | — |
| Reactant | 1,1-Dimethylethyl N-(5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamate | HCID 11514385 | — |
| Reactant | 4-bromo-N-(3-methoxyphenyl)-N-methylbenzenesulfonamide | HCID 62003284 | — |
| Reactant | 5-Iodo-2-tritylisoindoline | HCID 66726248 | — |
| Product | tert-Butyl-5-((4-(N-(3-methoxyphenyl)-N-methylsulfamoyl)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate | HCID 131733942 | 59% |
Reaction Steps
When tert-butyl 5-ethynyl-2,2-dimethyl-1,3-dioxan-5-ylcarbamate was substituted for 1-octyne and the product of Step B was substituted for 5-iodo-2-tritylisoindoline in Example 2, Step D, the similar process afforded the title compound in 59% yield, as a creamy paste. 1H-NMR (CDCl3) 1.45 (s, 3H); 1.46 (s, 9H); 1.49 (5, 3H); 1.58 (s, 2H); 2.63 (s, 2H); 3.13 (s, 3H); 3.75 (s, 3H); 3.96 (d, 2H, J=17.23 Hz), 4.07 (d, 2H, J=17.23 Hz); 6.54 (dd, 1H, J=1.66, 7.92 Hz), 6.69 (tr, 1H, J=2.18 Hz); 6.79 (dd, 1H, J=2.39, 10.68 Hz); 7.16 (tr, 1H, J=8.15 Hz); 7.47 (s, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09181182B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-8ffce183ff9b4336a235c886e0df4ef1 |
| Source note | uspto-grants-2015_11 |