HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Tert-butyl (r)-4-fluoro-3-[[[n-(benzyloxycarbonyl)serinyl]methylamino]methyl]benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Z-D-Ser-OH | HCID 489184 | — |
| Reactant | 1,1-Dimethylethyl 4-fluoro-3-[(methylamino)methyl]benzoate | HCID 11791275 | — |
| Solvent | dichloromethane N,N-dimethylformamide | HCID 22350042 | — |
| Product | Tert-butyl (r)-4-fluoro-3-[[[n-(benzyloxycarbonyl)serinyl]methylamino]methyl]benzoate | HCID 131723730 | 85.8% |
Reaction Steps
According to the procedure of Preparation 4(c), except using tert-butyl 4-fluoro-3-(methylaminomethyl)benzoate (4.00 g, 16.7 mmole), N-(benzyloxycarbonyl)-D-serine (4.00 g, 16.7 mmole), HOBt.H2O (2.3 g, 17 mmole), DCC (2.4 g, 11.6 mmole), and 1:1 DMF/CH2Cl2 (100 mL), the title compound (6.60 g, 79%) was prepared as a sticky foam following flash chromatography on silica gel (50% EtOAc/hexanes): MS (ES) m/e 461.1 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06503903B1 |
| Source dataset | uspto-grants-2003_01 |
| ORD ID | ord-b5975a095c5c4ae39efb7cd8c1aed1ae |
| Source note | uspto-grants-2003_01 |