Water → HCID 178499293, compound

HRID 1190034Notes

Reaction equation

HRID 1190034 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:35]2[CH2:40][CH2:39][C:38]([CH3:42])([CH3:41])[CH2:37][CH2:36]2)=[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]([CH:35]2[CH2:36][CH2:37][C:38]([CH3:41])([CH3:42])[CH2:39][CH2:40]2)=[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[CH2:12][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 178499294HCID 178499294, compound

Product 1

HCID 178499293HCID 178499293, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-(4,4-dimethyl-cyclohexyl)-3-{(trans-4-methyl-cyclohexanecarbonyl)-[trans-4-(4-trimethylsilanyl-[1,2,3]triazol-1-yl)cyclohexyl]-amino}-thiophene-2-carboxylic acid methyl ester (1.1 g, 1.8 mmol) in THF (4.4 ml) was added TBAF 1.0 M in THF (0.270 ml, 2.70 mmol). The reaction mixture was stirred for 24 h and treated with water and saturated ammonium chloride solution. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated under reduce pressure. The residue was purified by silica gel column chromatography (50% ethyl acetate/hexane to 100% ethyl acetate) to give 5-(4,4-Dimethyl-cyclohexyl)-3-[(trans-4-methyl-cyclohexanecarbonyl)-(trans-4-[1,2,3]triazol-1-yl-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester (0.534 g, 55%).

Workup

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

Sources & evidence

ORD record
ord-c14d49f55dbf4f6c958336b9f87f93df
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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