HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (R)-tert-butyl 3,3-dimethyl-1-(methylamino)-1-oxobutan-2-ylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | Methylamine hydrochloride | HCID 6364545 | — |
| Reactant | (2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acid | HCID 7005057 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (R)-tert-butyl 3,3-dimethyl-1-(methylamino)-1-oxobutan-2-ylcarbamate | HCID 57635611 | 77.7% |
Reaction Steps
To a cold solution of (R)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid (0.50 g, 2.16 mmol) in acetonitrile (8 mL) was added methylamine hydrochloride (0.48 g, 7.13 mmol), followed by DIEA (1.67 g, 12.9 mmol). The resulting mixture was stirred for 20 min and TBTU (0.76 g, 2.37 mmol) was added and the stirring continued overnight. The mixture was concentrated, diluted with EtOAc (30 mL) and washed successively with aqueous 5% KHSO4, saturated NaHCO3 solution and brine, dried over anhydrous Na2SO4, filtered and concentrated to provide Intermediate 30A (0.41 g, 77%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08431565B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-11760df5ec0a4cd9b722c20f57cf99f3 |
| Source note | uspto-grants-2013_04 |