Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethylamine | HCID 8021 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-Methyl-1,2-dithiolane-4-carboxylic acid | HCID 20069311 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethylacetate heptane | HCID 21899848 | — |
| Product | HCID 45111295 | HCID 45111295 | — |
Reaction Steps
5 ml of anhydrous dichloromethane and 0.1 ml of anhydrous DMF are added to 2.26 mmol of Compound 1. The mixture is cooled to 0° C. and 2.7 mmol of oxalyl chloride are added. The mixture is stirred at 20° C. and then added at 0° C. to a mixture of 2.26 mmol of diethylamine, 5 ml of anhydrous dichloromethane and 6.8 mmol of diisopropylethylamine. The reaction medium is stirred for 3 hours at 20° C. When the reaction is complete, the medium is diluted in 50 ml of dichloromethane and then washed with 2×30 ml of water and 1×50 ml of saturated NH4Cl solution, dried over Na2SO4 and evaporated to dryness on a rotavapor. After flash chromatography (eluent: heptane/EtOAc), Compound 18 is isolated in the form of a yellow oil (48% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08617524B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-91ea94b8d4124a3dbed2cbc620bf0ce1 |
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| Source note | uspto-grants-2013_12 |
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