Sodium Hydroxide → HCID 59294530, compound

HRID 1877404Notes

Reaction equation

HRID 1877404 reaction equation
C[O:2][C:3](=[O:42])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([C:25]([C:27]3[C:28]([O:33][C:34]4[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:35]=4[Cl:41])=[N:29][CH:30]=[CH:31][CH:32]=3)=[O:26])[CH2:17][CH2:16]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.[OH-].[Na+]>C(O)C>[Cl:41][C:35]1[CH:36]=[CH:37][C:38]([Cl:40])=[CH:39][C:34]=1[O:33][C:28]1[C:27]([C:25]([N:18]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:15]([S:12]([C:9]3[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:42])=[O:2])=[CH:7][CH:8]=3)(=[O:14])=[O:13])[CH2:16][CH2:17]2)=[O:26])=[CH:32][CH:31]=[CH:30][N:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67367390HCID 67367390, compound

Product 1

HCID 59294530HCID 59294530, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 3-(4-{4-[2-(2,5-dichloro-phenoxy)-pyridine-3-carbonyl]-3,4-dihydro-2H-quinoxaline-1-sulfonyl}-phenyl)-propionic acid methyl ester (36 mg, 0.058 mmol, 1.0 equiv) in ethanol (1 mL) was added a 1 M solution of sodium hydroxide (120 μL, 0.12 mmol, 2.0 equiv; [CAS RN 1310-73-2]) and the reaction mixture stirred at rt over night. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase (Xterra® PrepMSC 18, 5 μm, 19×50 mm column equipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps, a Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) eluting with a gradient of acetonitrile/water provided 4.5 mg (13%) of the title compound as a light yellow powder. MS (ISP): 612.1 [M+H]+.

Workup

  1. customRemoval of the solvent
  2. customunder reduced pressure and purification by preparative HPLC on reversed phase (Xterra® PrepMSC 18, 5 μm, 19×50 mm column
  3. customequipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps
  4. washa Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) eluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-ace0e8e5342f45549d9bddb7dbe3c5f7
Source dataset
uspto-grants-2012_11
Patent number
US08309734B2

Reaction notes

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