Tetrahydrofuran → HCID 20740230, compound

HRID 1883142Notes

Reaction equation

HRID 1883142 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([OH:13])=O.[C:14]([C@@H:16]([NH:21][C:22]([C@@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@@H:25]1[NH-:30])=[O:23])[CH2:17][CH2:18]SC)#[N:15].O[O:32][S:33]([O-:35])=O.[K+].[CH2:37]1COCC1>>[C:14]([C@@H:16]([NH:21][C:22]([C@@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@@H:25]1[NH:30][C:11]([C:3]1[N:2]([CH3:1])[C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:13])=[O:23])[CH2:17][CH2:18][S:33]([CH3:37])(=[O:35])=[O:32])#[N:15]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 276951H-Indole-2-carboxylic acid, 1-methyl-HCID 23707502Potassium hydroxy sulfiteHCID 86759485HCID 86759485, compound2×

Product 1

HCID 20740230HCID 20740230, compoundYield 81%

Procedure

To a solution of 1-methyl-1H-indole-2-carboxylic acid [((1S,2R)-2-((S)-1-cyano-3-methylsulfanyl-propylcarbamoyl)-cyclohexyl]-amide (compound 3-2, 203 mg, 0.492 mmol) in 20 mL of THF, was added Oxone™ (390 mg, 0.634 mmol). The reaction mixture was stirred at ambient temperature for 2 hours, filtered through a pad of celite, dried with sodium sulfate, filtered, concentrated, and purified by column chromatography (5:95, MeOH/CH2Cl2) to give 178 mg (81%) of 1-methyl-1H-indole-2-carboxylic acid [(1S,2R)-2-((S)-1-cyano-3-methanesulfonyl-propylcarbamoyl)-cyclohexyl]-amide as a yellow amorphous solid. MS: 445 (M+H+).

Workup

  1. filtrationfiltered through a pad of celite
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography (5:95, MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3833c16e22494857a3f13a1ba44789f5
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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