TBAF tetrahydrofuran → HCID 86626882, compound

HRID 604136Notes

Reaction equation

HRID 604136 reaction equation
[F:1][C:2]([F:55])([F:54])[C:3]1[CH:4]=[C:5]([CH:47]=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:49]=1)[CH2:6][N:7]([CH2:23][C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=1[NH:34][C@H:35]([C:38](C)(C)[O:39][SiH2]C(C)(C)C)[CH2:36][CH3:37])[C:8]1[N:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:10][N:9]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>O1CCCC1>[F:55][C:2]([F:1])([F:54])[C:3]1[CH:4]=[C:5]([CH:47]=[C:48]([C:50]([F:51])([F:52])[F:53])[CH:49]=1)[CH2:6][N:7]([CH2:23][C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=1[NH:34][C@H:35]([CH2:38][OH:39])[CH2:36][CH3:37])[C:8]1[N:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][N:13]=1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 131728752HCID 131728752, compound

Product 1

HCID 86626882HCID 86626882, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-[2-((3,5-bis-trifluoromethyl-benzyl)-{2-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propylamino]-5-trifluoromethyl-benzyl}-amino)-pyrimidin-5-yloxy]-butyrate (183 mg) is dissolved in tetrahydrofuran (3 mL) and thereto is added 1M-tetrabutylammonium fluoride/tetrahydrofuran solution (1 ml) and the mixture is stirred at room temperature for 20 minutes. The reaction solution is concentrated under reduced pressure and thereto is added a saturated brine, and the mixture is extracted with ethyl acetate. The organic layer is washed twice with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→2:1) to give ethyl 4-(2-{(3,5-bis-trifluoromethyl-benzyl)-[2-((S)-1-hydroxymethyl-propylamino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-5-yloxy)-butyrate (93 mg). MS (m/z): 697 [M+H]+

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. additionis added a saturated brine
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe organic layer is washed twice with a saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→2:1)

Sources & evidence

ORD record
ord-0d40cdbe9b294edcbf4587df84f4fdba
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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