HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Tert-butyl (r)-4-fluoro-3-[[[n-(benzyloxycarbonyl)serinyl]-phenethylamino]methyl]benzoate
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 23505567 | HCID 23505567 | — |
| Solvent | dichloromethane N,N-dimethylformamide | HCID 22350042 | — |
| Product | Tert-butyl (r)-4-fluoro-3-[[[n-(benzyloxycarbonyl)serinyl]-phenethylamino]methyl]benzoate | HCID 131723732 | 41.1% |
Reaction Steps
According to the procedure of Preparation 4(c), except using tert-butyl 4-fluoro-3-[(phenethylamino)methyl]benzoate (5.00 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 (3.44 g, 41%) 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 7.31-8.18 (m, 2 H), 7.19-7.29 (m, 11 H), 4.86-5.11 (m, 4 H), 4.33-4.79 (m, 3 H), 3.49-3.80 (m, 4 H), 1.51 (s, 9 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06503903B1 |
| Source dataset | uspto-grants-2003_01 |
| ORD ID | ord-6f9b9a0a5d2e4512a8a83ad909d63a38 |
| Source note | uspto-grants-2003_01 |