Tetrabutylammonium Fluoride → HCID 44125593, compound

HRID 1913509Notes

Reaction equation

HRID 1913509 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([S:30][CH2:31][C:32]3[N:33]=[C:34]([C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=4)[S:35][CH:36]=3)=[C:8]([C:28]#[N:29])[C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][Si](C(C)(C)C)(C)C)=[CH:13][CH:12]=2)[N:4]([CH2:44][C:45]([O:47][CH3:48])=[O:46])[C:3]=1[C:49]([O:51][CH3:52])=[O:50].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([S:30][CH2:31][C:32]3[N:33]=[C:34]([C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=4)[S:35][CH:36]=3)=[C:8]([C:28]#[N:29])[C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][OH:20])=[CH:13][CH:12]=2)[N:4]([CH2:44][C:45]([O:47][CH3:48])=[O:46])[C:3]=1[C:49]([O:51][CH3:52])=[O:50]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58097243HCID 58097243, compound

Product 1

HCID 44125593HCID 44125593, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

19 mg (0.024 mmol) of the compound from Example 33A were initially charged in 1 ml of THF, and 0.122 ml (0.122 mmol) of a 1N solution of tetrabutylammonium fluoride in THF were added. The reaction mixture was stirred at RT for 2 h and then diluted with ethyl acetate. The mixture was washed with saturated aqueous sodium bicarbonate solution. The organic phase was dried over sodium sulfate and concentrated, and the residue was purified by preparative HPLC (Chromasil, water/acetonitrile). This gave 15 mg of the product, which were purified by preparative thin-layer chromatography (dichloromethane/methanol=20/1).

Workup

  1. washThe mixture was washed with saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe residue was purified by preparative HPLC (Chromasil, water/acetonitrile)
  5. customThis gave 15 mg of the product, which were purified by preparative thin-layer chromatography (dichloromethane/methanol=20/1)

Sources & evidence

ORD record
ord-1662234d35644b13a4d61dca40b64be6
Source dataset
uspto-grants-2013_12
Patent number
US08609686B2

Reaction notes

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