Tetrabutylammonium Fluoride → HCID 60083626, compound

HRID 1883154Notes

Reaction equation

HRID 1883154 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]1[NH:13][C:14]([C:16]1[N:17]([CH2:26][CH2:27][O:28]C[Si](C(C)C)(C(C)C)C(C)C)[C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[C:20]([Cl:25])[CH:19]=2)=[O:15])=[O:6])#[N:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]1[NH:13][C:14]([C:16]1[N:17]([CH2:26][CH2:27][OH:28])[C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[C:20]([Cl:25])[CH:19]=2)=[O:15])=[O:6])#[N:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86591898HCID 86591898, compound

Product 1

HCID 60083626HCID 60083626, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 140 mg (0.25 mmol) of 6-chloro-1-{2-[(triisopropylsilanyl)-methoxy]-ethyl}-1H-indole-2-carboxylic acid [(1S,2R)-2-(cyanomethyl-carbamoyl)-cyclohexyl]-amide dissolved in 20 mL THF was added 66 mg (0.25 mmol) of tetrabutylammonium fluoride (1.0 M in THF). The reaction mixture was stirred at room temperature for several hours, concentrated, and purified by column chromatography eluting with 70% ethyl acetate in hexane to provide 50 mg of 6-chloro-1-(2-hydroxy-ethyl)-1H-indole-2-carboxylic acid [(1S,2R)-2-(cyanomethyl-carbamoyl)-cyclohexyl]-amide. HPLC: 98% pure, yield: 50%, MS: 403 (M+H+).

Workup

  1. concentrationconcentrated
  2. custompurified by column chromatography
  3. washeluting with 70% ethyl acetate in hexane

Sources & evidence

ORD record
ord-70b3e690dbb14bcf8712a404b746f145
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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