Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 58361501 | HCID 58361501 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 58361511 | HCID 58361511 | 81.6% |
Reaction Steps
To a solution of compound 18 (190 mg, 0.435 mmol) in MeOH (1 mL) were added methyl amine (0.04 mL, 0.462 mmol), HOAc (0.005 mL), and NaBH(OAc)3 (200 mg, 0.943 mmol). The reaction was stirred at 25° C. for 20 h. After the reaction was complete, 1 N HCl (0.1 mL) was added to the reaction mixture and then neutralized with saturated aq. NaHCO3. The resulting mixture was extracted with EtOAc, and the organic layers were pooled, washed with brine, and dried over Na2SO4. Solvent was removed in vacuo to afford 19 (160 mg, 0.355 mmol, 81%) as a colorless oil, which was used without further purification. MS-ESI (m/z): [M+H]+ calculated for C19H20BrN2O4S, 451.03 (79Br) and 453.03 (81Br); found 450.89 (79Br) and 453.01 (81Br).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07923562B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-9f7887113da34546ad01625c8ef0307d |
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| Source note | uspto-grants-2011_04 |
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