HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Hydroxide → HCID 67606700, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Z-N-Me-Ala-OH | HCID 7016365 | — |
| 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 | 4-(2-Amino-3,3-dimethyl-butyryl)-3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester | HCID 67506208 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 67606700 | HCID 67606700 | — |
Reaction Steps
A stirred solution of Cbz-N(Me)Ala-OH (7.85 g, 7.70 mmol), HATU (2.95 g, 7.70 mmol), and DIPEA (1.60 mL, 9.10 mmol) in NMP (20 mL) was cooled to 0° C. and amine 47 (7.02 mmol) in NMP (20 mL) was added. The solution was allowed to warm to ambient temperature. After 13 h, the reaction mixture was cooled to 0° C. and 1N NaOH (10 mL) was added. The reaction mixture was diluted with water and extracted with Et2O. The combined organic extracts were washed successively with water, 1N HCl, 10% H3PO4, water, NaHCO3, water, and brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to afford 4.5 g (96%, 2 steps) of 48 as a white foam which was used without further purification. Mass spectrum, m/z [691.2] (M+Na)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08415486B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-30fadb7d5aae494687c8657439fc305e |
| Source note | uspto-grants-2013_04 |