Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sulfuryl chloride | HCID 24648 | — |
| Reactant | methyl L-prolinate hydrochloride | HCID 2733200 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 159525-92-5 | HCID 10036702 | 87.8% |
Reaction Steps
A solution of L-proline methyl ester hydrochloride (0.33 g, 0.002 mole) in toluene (5 ml), dichloromethane (2 ml) and triethylamine (0.6 ml, 0.004 mole) was added dropwise over a period of 3 minutes to a cold (−20° C.) solution of sulfuryl chloride (0.32 ml, 0.0039 mole) in toluene. The mixture was stirred an additional 45 minutes at −20° C. The reaction was filtered and the solvent was removed under reduced pressure to give the title compound (0.40 g). 1H NMR (300 MHz, CDCl3) δ 2.13 (m, 2 H) 2.32 (m, 2 H) 3.58 (m, 1 H) 3.75 (m, 1 H) 3.79 (s, 3 H) 4.40 (dd, J=8.82, 4.04 Hz, 1 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07902203B2 |
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| Source dataset | uspto-grants-2011_03 |
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| ORD ID | ord-573d516794b743f1a45bbde0ca93b9ed |
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| Source note | uspto-grants-2011_03 |
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