HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Phenyl 5-tert-butyl-2-methoxy-3-(methylsulfonamido)phenylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Phenyl chloroformate | HCID 15891 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide | HCID 10214710 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Cyclohexane | HCID 8078 | — |
| Product | Phenyl 5-tert-butyl-2-methoxy-3-(methylsulfonamido)phenylcarbamate | HCID 86275692 | 97.2% |
Reaction Steps
Phenyl chloroformate (0.5 mL, 3.99 mmol) was added to a stirred solution of N-(3-amino-5-(tert-butyl)-2-methoxyphenyl)methanesulfonamide (see, for example, Cirillo, P. F. et al., WO 2002/083628, 24 Oct. 2002; 1 g, 3.67 mmol) and NaHCO3 (620 mg, 7.38 mmol) in THF (10 mL) and DCM (10 mL). The mixture was stirred for 2 h then water (20 mL) was added. The organic layer was separated, dried (MgSO4), filtered and evaporated to furnish a brown foam, which was stirred in cyclohexane (20 mL) to afford the sub-title compound (1.4 g) as a colourless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08927563B2 |
| Source dataset | uspto-grants-2015_01 |
| ORD ID | ord-80e8ce346114485abccb8bb5bdcbb363 |
| Source note | uspto-grants-2015_01 |