Methanol → HCID 178494217, compound

HRID 1944752Notes

Reaction equation

HRID 1944752 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]([NH:19][S:20]([C:23]3[CH:24]=[N:25][C:26](Cl)=[C:27]([Br:29])[CH:28]=3)(=[O:22])=[O:21])[CH2:15][CH2:14]2)=[O:12])[CH3:9])=[CH:4][CH:3]=1.[CH3:31][OH:32]>C[O-].[Na+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]([NH:19][S:20]([C:23]3[CH:24]=[N:25][C:26]([O:32][CH3:31])=[C:27]([Br:29])[CH:28]=3)(=[O:22])=[O:21])[CH2:15][CH2:14]2)=[O:12])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 178462127HCID 178462127, compound

Product 1

HCID 178494217HCID 178494217, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

Trans-4-(5-Bromo-6-chloro-pyridine-3-sulfonylamino)-cyclohexanecarboxylic acid [(R)-1-(4-fluoro-phenyl)-ethyl]-amide (Example 144, 484 mg, 0.933 mmol) was dissolved in a solution of NaOMe in MeOH (0.5M, 28 ml, 13.99 mmol). The reaction mixture was stirred overnight at room temperature. LCMS indicated that the reaction was complete and it was concentrated in vacuo then taken up in EtOAc and purified via column chromatography using a biotage SP1, 40+M column, with 50% EtOAc in heptane as calculated gradient to yield the title compound as a white solid (313 mg, 65%). [M+H]=516.0

Workup

  1. concentrationit was concentrated in vacuo
  2. custompurified via column chromatography

Sources & evidence

ORD record
ord-bad2d5482f844b4ca83745d8a0cff896
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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