HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → methyl(7R)-7-[[N-(tert-butoxycarbonyl)-beta-alanyl](methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-((1,1-dimethylethoxy)carbonyl)-beta-alanine | HCID 76809 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | methyl(7R)-14-cyclohexyl-7-(methylamino)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate | HCID 66674181 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | methyl(7R)-7-[[N-(tert-butoxycarbonyl)-beta-alanyl](methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate | HCID 66674302 | — |
Reaction Steps
A solution of methyl(7R)-14-cyclohexyl-7-(methylamino)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (prepared as described in Example 1, Step 5) and N-(tert-butoxycarbonyl)-β-alanine (1.2 eq) in DCM (0.15 M) was treated with HATU (1.3 eq.) and DIPEA (3 eq.) and the resulting mixture was stirred for 90 min at RT. The reaction was diluted with EtOAc and the combined organic layers were washed with 1N HCl (aq), sat aq NaHCO3 then brine, before being dried (Na2SO4), filtered and concentrated in vacuo. The product was used directly in the next step without further purification. (ES+) m/z 590 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08101595B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-e6154159237744ed915756e12a14e44f |
| Source note | uspto-grants-2012_01 |