HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → tert-Butyl (3-(methoxyimino)-3-(4-methoxyphenyl)-propanamido)(methylthio)methylenecarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | CarbaMic acid, [iMino(Methylthio)Methyl]-, 1,1-diMethylethyl ester (9CI) | HCID 54237411 | — |
| Reactant | 3-(Methoxyimino)-3-(4-methoxyphenyl)propanoic acid | HCID 58984532 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | tert-Butyl (3-(methoxyimino)-3-(4-methoxyphenyl)-propanamido)(methylthio)methylenecarbamate | HCID 72481141 | 88.6% |
Reaction Steps
A mixture of 3-(methoxyimino)-3-(4-methoxyphenyl)propanoic acid (223 mg), tert-butyl amino(methylthio)methylenecarbamate (190 mg), EDAC.HCl (384 mg), DMAP (122 mg) and triethylamine (0.56 mL) in dichloromethane (3 mL) was stirred at room temperature for 12 h. The crude reaction mixture was purified directly by preparative TLC eluting with 35% ethyl acetate/75% hexanes to give the title compound as a yellowish oil (350 mg). HPLC retention time: 2.42 min (method A). MS (ESI) (M+Na)+ 418.18.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07390925B2 |
| Source dataset | uspto-grants-2008_06 |
| ORD ID | ord-82c15c6d766446c481efedaa853fc77c |
| Source note | uspto-grants-2008_06 |