Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | L-(+)-Cysteine | HCID 5862 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Methyl chloroformate | HCID 6586 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 22940519 | HCID 22940519 | 75.2% |
Reaction Steps
A solution of L-cysteine (50 mg, 0.413 mmol) in methanol (0.4 mL) was treated with 1N NaOH (0.45 mL, 0.45 mmol) and methyl iodide (28.3 μL, 0.45 mmol) at 0° C. The mixture was warmed to 25° C. over 16 h, recooled to 0° C., and treated with 3N NaOH (0.45 μL, 1.3 mmol) and methyl chloroformate (64 μL, 0.83 mmol) at 25° C. for 4 h. The mixture was acidified with 2N HCl, and partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, and dried over MgSO4 and filtered. The solvents were evaporated to give the crude title compound (60 mg, 75%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07834043B2 |
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| Source dataset | uspto-grants-2010_11 |
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| ORD ID | ord-e02375f08d614508b0ded4ae5871421a |
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| Source note | uspto-grants-2010_11 |
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