Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | tert-Butyldimethylsilane | HCID 5072427 | — |
| Reactant | HCID 131715957 | HCID 131715957 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 131715956 | HCID 131715956 | — |
Reaction Steps
To a dichloromethane solution (1.0 ml) of palladium (II) acetate (8.0 mg, 0.04 mmol) and triethylamine (16 μl, 0.12 mmol), t-butyldimethylsilane (187 μl, 1.1 mmol) was added and the mixture was stirred for 15 minutes at room temperature in an argon atmosphere. To the resulting black suspension, a dichloromethane solution (1.0 ml) of N-allyloxycarbonylallylglycine methyl ester (150 mg, 0.75 mmol) was added and the mixture was stirred for an additional 20 hours. After a saturated aqueous solution of ammonium chloride was added to quench the reaction, extraction with ether was conducted and the ether layer was dried over anhydrous magnesium sulfate and filtered. By distilling off the solvent, N-t-butyldimethylsilyloxycarbonylallylglycine was obtained in an amount of 184 mg (yield, 90%). The physical data for this compound were in agreement with those reported in Examples 3 and 11.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04837349 |
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| Source dataset | uspto-grants-1989_06 |
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| ORD ID | ord-87b0aa67792b46f3a2b4ccf5093cb6ee |
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| Source note | uspto-grants-1989_06 |
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