Water → Phenyl 5-tert-butyl-2-methoxy-3-(methylsulfonamido)phenylcarbamate

HRID 1423256Notes

Reaction equation

HRID 1423256 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1[C:13]([O:27][CH3:28])=[C:14]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH:15]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:17]=1.C([O-])(O)=O.[Na+].O>C1COCC1.C(Cl)Cl.C1CCCCC1>[C:5]1([O:4][C:2](=[O:3])[NH:11][C:12]2[CH:17]=[C:16]([C:18]([CH3:20])([CH3:21])[CH3:19])[CH:15]=[C:14]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[C:13]=2[O:27][CH3:28])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 962WaterHCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide

Product 1

HCID 86275692Phenyl 5-tert-butyl-2-methoxy-3-(methylsulfonamido)phenylcarbamateYield 97.2%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Procedure

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.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto furnish a brown foam, which

Sources & evidence

ORD record
ord-80e8ce346114485abccb8bb5bdcbb363
Source dataset
uspto-grants-2015_01
Patent number
US08927563B2

Reaction notes

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