HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → tert-Butyl (3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3-oxopropyl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 2,2-Dimethyl-1,3-dioxane-4,6-dione | HCID 16249 | — |
| Reactant | N-((1,1-dimethylethoxy)carbonyl)-beta-alanine | HCID 76809 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | tert-Butyl (3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3-oxopropyl)carbamate | HCID 68556020 | 85.8% |
Reaction Steps
EDCI (59.39 g, 310.8 mmol) was added at 0° C. to a stirred solution of 3-(tert-butoxycarbonylamino)propanoic acid (I-59a: 49 g, 258.9 mmol), meldrum's acid (41.05 g, 284.8 mmol) and DMAP (47.4 g, 388.5 mmol) in DCM (490 mL) and the resulting reaction mass was allowed to stir at room temperature overnight. The reaction was monitored by TLC (10% methanol in CHCl3). The reaction mass was washed with 5% KHSO4 solution and separated the layers. The organic layer was dried over Na2SO4 and concentrated to afford 70 g of the product (85.8% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08946260B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-3330c8da210f442587698a9e7150b316 |
| Source note | uspto-grants-2015_02 |