HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → (+/-)-N-[2-[4-(Triisopropylsilyloxy)benzyl]-3-(carbomethoxy)propionyl]serine benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Benzyl L-serinate--hydrogen chloride (1/1) | HCID 12930233 | — |
| Reactant | Methyl (+/-)-3-carboxy-4-[4-(triisopropylsilyloxy)phenyl]butanoate | HCID 20775649 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (+/-)-N-[2-[4-(Triisopropylsilyloxy)benzyl]-3-(carbomethoxy)propionyl]serine benzyl ester | HCID 20775644 | 79% |
Reaction Steps
To a solution of methyl (±)-3-carboxy-4-[4-(triisopropylsilyloxy)phenyl]butanoate (5.00 g, 12.67 mmole) in dry DMF (60 mL) at RT was added serine benzyl ester hydrochloride (3.52 g, 15.21 mmole), HOBt (2.06 g, 15.21 mmole), Et3N (5.3 mL, 38.01 mmole), and EDC (2.92 g, 15.21 mmole). After 18 hr the mixture was concentrated. The residue was chromatographed on silica gel (80% EtOAc/hexanes) to give the title compound (5.76 mg, 79%) as a pale yellow oil: MS (ES) m/e 572 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06881736B1 |
| Source dataset | uspto-grants-2005_04 |
| ORD ID | ord-63d9e70464304b90b3186e55243a83cd |
| Source note | uspto-grants-2005_04 |