HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | N-(tert-Butoxycarbonyl)-L-cyclohexylglycine | HCID 7004938 | — |
| 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 | Hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester | HCID 67281633 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | 4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester | HCID 67281489 | 106.3% |
Reaction Steps
A solution of Boc-L-cyclohexylglycine (257 mg, 1 mmol) in NMP (5 mL) was cooled to 0° C. and treated with HATU (380 mg, 1 mmol) followed by DIPEA (0.3 mL, 1.7 mmol). After 10 min, 15 (309 mg, 1.0 mmol) in NMP (5 mL) was added. The reaction mixture was allowed to warm to ambient temperature overnight. The solution was diluted with EtOAc, washed successively with 1M HCl, saturated NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated to afford 16 as an orange-colored foam (578 mg) which was used without further purification. Mass spectrum, m/z [544.4] (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08481495B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-a34612f279514ad5b5d29c3cc47dcaac |
| Source note | uspto-grants-2013_07 |