Sodium Hydroxide → HCID 86687170, compound

HRID 1402333Notes

Reaction equation

HRID 1402333 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[C:5]([O:19][CH3:20])=[C:6]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:7]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:9]=1.Cl[C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23]>>[Cl:27][C:26]([Cl:29])([Cl:28])[CH2:25][O:24][C:22](=[O:23])[NH:3][C:4]1[CH:9]=[C:8]([C:10]([CH3:12])([CH3:13])[CH3:11])[CH:7]=[C:6]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[C:5]=1[O:19][CH3:20]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide

Product 1

HCID 86687170HCID 86687170, compoundYield 75%

Procedure

NaOH (199 mg, 4.97 mmol) was added to an ice-bath cooled solution of N-[3-amino-5-(1,1-dimethylethyl)-2-methoxyphenyl]-methane sulfonamide (for reference procedure see for example WO2010026096, which is incorporated herein by reference in its entirety; 500 mg, 1.84 mmol). The ice bath was removed and complete dissolution of reagents occurred. 2,2,2-trichloroethyl chloroformate (380 μL, 2.76 mmol) was added and the reaction mixture was warmed to RT and stirred for 90 min. The reaction mixture was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc (×3) and the combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by FCC on silica, using a gradient of 0-60% EtOAc in cyclohexane, to afford the title compound (620 mg, 75%) as a white solid. LCMS (Method 1): Rt 3.98 min, m/z 445, 447, 449 [MH+].

Workup

  1. customThe ice bath was removed
  2. dissolutioncomplete dissolution of reagents
  3. customThe reaction mixture was partitioned between EtOAc and water
  4. extractionThe aqueous phase was extracted with EtOAc (×3)
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was purified by FCC on silica

Sources & evidence

ORD record
ord-37b2557c300d437b9d00e18f78605692
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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