Potassium Carbonate → (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(4-(methylsulfonamido)benzylcarbamoyloxy)ethyl)pyridine 1-oxide

HRID 1776465Notes

Reaction equation

HRID 1776465 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:46])[CH:5]=[C:6]([Cl:45])[C:7]=1[CH2:8][C@@H:9]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH:37]([F:39])[F:38])=[C:32]([O:40][CH2:41][CH:42]2[CH2:44][CH2:43]2)[CH:31]=1)[O:10][C:11](=[O:29])[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N:20](S(C)(=O)=O)[S:21]([CH3:24])(=[O:23])=[O:22])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:46])[CH:5]=[C:6]([Cl:45])[C:7]=1[CH2:8][C@@H:9]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH:37]([F:38])[F:39])=[C:32]([O:40][CH2:41][CH:42]2[CH2:44][CH2:43]2)[CH:31]=1)[O:10][C:11](=[O:29])[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 131734758(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(4-(N-(methylsulfonyl)methylsulfonamido) benzylcarbamoyloxy)ethyl)pyridine 1-oxide

Product 1

HCID 86679421(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(4-(methylsulfonamido)benzylcarbamoyloxy)ethyl)pyridine 1-oxideYield 46.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(4-(N-(methylsulfonyl)methylsulfonamido)benzylcarbamoyloxy)ethyl)pyridine 1-oxide (218 mg, 0.301 mmol) was dissolved in MeOH (10 ml), and potassium carbonate (125 mg, 0.903 mmol) was added. The mixture was stirred at 60° C. for 1 hour. The solvent was removed under vacuum, and the crude material was portioned between water and EtOAc. The organic layer was dried over Na2SO4, and the solvent was evaporated affording a crude material that was purified by flash chromatography on silica gel (DCM:MeOH 100:0.2) affording the desired product (90 mg, 0.139 mmol, 46.3% yield, MS/ESI+ 645.85 [MH]+ [αD]=−32.16, c 0.523, DCM).

Workup

  1. customThe solvent was removed under vacuum
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent was evaporated
  4. customaffording a crude material that
  5. customwas purified by flash chromatography on silica gel (DCM:MeOH 100:0.2)

Sources & evidence

ORD record
ord-ef61442f28954886a20bda1f5de8630c
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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