HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 86588818, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Z-D-Ser-OH | HCID 489184 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 23505584 | HCID 23505584 | — |
| Solvent | dichloromethane N,N-dimethylformamide | HCID 22350042 | — |
| Product | HCID 86588818 | HCID 86588818 | 19.4% |
Reaction Steps
According to the procedure of Preparation 4 (c), except using tert-butyl 4-fluoro-3-(benzylaminomethyl)benzoate (4.80 g, 15.2 mmole), N-(benzyloxycarbonyl)-D-serine (3.83 g, 16 mmole), HOBt.H2O (2.16 g, 16 mmole), Et3N (2.24 mL, 16 mmole), EDC.HCl (3.07 g, 16 mmole), and 1:1 DMF/CH2Cl2 (75 mL), the title compound (1.58 g, 19%) was prepared as a thick oil following flash chromatography on silica gel (40% EtOAc/hexanes): 1H NMR (300 MHz, DMSO-d6) mixture of amide rotamers δ 7.39-8.18 (m, 2H), 7.18-7.37 (m, 11H), 4.25-5.11 (m, 7H), 3.33-4.04 (m, 2H), 1.53 (s, 9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06765005B2 |
| Source dataset | uspto-grants-2004_07 |
| ORD ID | ord-41e0e393211c447ebf82e6fcad621144 |
| Source note | uspto-grants-2004_07 |