HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → {[2-(Tert-butoxycarbonylamino)-ethyl]-methyl-amino}-acetic acid benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | tert-Butyl N-(2-bromoethyl)carbamate | HCID 4103526 | — |
| Reactant | 4-Methylbenzene-1-sulfonic acid--benzyl N-methylglycinate (1/1) | HCID 12210899 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | {[2-(Tert-butoxycarbonylamino)-ethyl]-methyl-amino}-acetic acid benzyl ester | HCID 59650730 | 38.2% |
Reaction Steps
500 mg (1.42 mmol) of sarcosine benzyl ester p-toluenesulfonate, 478 mg (2.13 mmol) of 2-(tert-butoxycarbonylamino)-ethyl bromide, and 0.25 mL (2.13 mmol) of diisopropyl-ethylamine were dissolved in methylene chloride (10 mL), and then stirred at room temperature for approximately three days. After completion of the reaction, the reaction solution was concentrated and the residue obtained was purified by silica gel column chromatography (ethyl acetate) to yield 175 mg (38%) of {[2-(tert-butoxycarbonylamino)-ethyl]-methyl-amino}-acetic acid benzyl ester as a colorless viscous oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08022047B2 |
| Source dataset | uspto-grants-2011_09 |
| ORD ID | ord-8aa04aed8f674ce49ce09455ac4e5e70 |
| Source note | uspto-grants-2011_09 |