HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 57945067, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methyl L-tert-leucinate | HCID 11309583 | — |
| Reactant | Pyridin-2-yl 1,1,1-trifluoro-2-methylpropan-2-yl carbonate | HCID 23595245 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 57945067 | HCID 57945067 | 99.4% |
Reaction Steps
To an ice-cooled solution of (S)-methyl 2-amino-3,3-dimethylbutanoate (0.411 g, 2.262 mmol) in DCM (20 mL) was added N,N-Diisopropylethylamine (1.182 mL, 6.79 mmol). The formed solution was stirred for 5 min before addition of carbonic acid pyridin-2-yl ester 2,2,2-trifluoro-1,1-dimethyl-ethyl ester (1.24 g, 4.98 mmol, from step 1a) in DCM (10 mL). The final light yellow solution was stirred at room temperature overnight. The reaction mixture was washed with 5% citric acid aqueous solution, 0.1 M NaOH aqueous solution, and brine, then dried over Na2SO4, filtered, and evaporated to dryness. The residue was purified by silica gel column, eluted with (4:1) hexane-EtOAc to afford a colorless oil as the product (673 mg, 99%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07888464B2 |
| Source dataset | uspto-grants-2011_02 |
| ORD ID | ord-ac93bf84522f47d9b091fbb6b4eb27d4 |
| Source note | uspto-grants-2011_02 |