Water → HCID 178499340, compound

HRID 244908Notes

Reaction equation

HRID 244908 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:35]#[C:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:8][C:9]=1[N:10]([C:26]([C@H:28]1[CH2:33][CH2:32][C@H:31]([CH3:34])[CH2:30][CH2:29]1)=[O:27])[C@H:11]1[CH2:16][CH2:15][C@H:14]([N:17]2[CH:21]=[C:20]([Si](C)(C)C)[N:19]=[N:18]2)[CH2:13][CH2:12]1)=[O:4].CCCC[N+](CCCC)(CCCC)CCCC.[F-].O.[Cl-].[NH4+]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:35]#[C:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[CH:8][C:9]=1[N:10]([C:26]([C@H:28]1[CH2:29][CH2:30][C@H:31]([CH3:34])[CH2:32][CH2:33]1)=[O:27])[C@H:11]1[CH2:12][CH2:13][C@H:14]([N:17]2[CH:21]=[CH:20][N:19]=[N:18]2)[CH2:15][CH2:16]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 178499341HCID 178499341, compound

Product 1

HCID 178499340HCID 178499340, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-(3,3-dimethyl-but-1-ynyl)-3-{(trans-4-methyl-cyclohexanecarbonyl)-[trans-4-(4-trimethylsilanyl-[1,2,3]triazol-1-yl)-cyclohexyl]-amino}-thiophene-2-carboxylic acid methyl ester (0.48 g, 0.82 mmol) in THF (2.0 ml) is added TBAF 1.0 M in THF (1.23 ml, 1.23 mmol). The reaction mixture is stirred for 24 h and treated with water and saturated ammonium chloride solution. The aqueous layer is extracted with ethyl acetate. The organic layer is washed with brine, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (50% ethyl acetate/hexane to 100% ethyl acetate) to give 5-(3,3-dimethyl-but-1-ynyl)-3-[(trans-4-methyl-cyclohexanecarbonyl)-(trans-4-[1,2,3]triazol-1-yl-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester.

Workup

  1. extractionThe aqueous layer is extracted with ethyl acetate
  2. washThe organic layer is washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (50% ethyl acetate/hexane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-197134325adb4d64982a2b7d1d43a6e3
Source dataset
uspto-grants-2014_02
Patent number
US08658674B2

Reaction notes

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