Tetrabutylammonium Fluoride → HCID 89624255, compound

HRID 2282555Notes

Reaction equation

HRID 2282555 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:19]([C:23]1[CH:24]=[C:25]([NH:35][C:36]([NH:38][C@@H:39]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C@H:42]([O:49][C:50]3[CH:51]=[CH:52][C:53]4[N:54]([C:56]([C@@H:59]5[CH2:63][CH2:62][CH2:61][N:60]5[CH2:64][CH2:65][CH2:66][O:67][Si](C(C)C)(C(C)C)C(C)C)=[N:57][N:58]=4)[CH:55]=3)[CH2:41][CH2:40]2)=[O:37])[N:26]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[N:27]=1)([CH3:22])([CH3:21])[CH3:20]>C1COCC1>[C:19]([C:23]1[CH:24]=[C:25]([NH:35][C:36]([NH:38][C@@H:39]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C@H:42]([O:49][C:50]3[CH:51]=[CH:52][C:53]4[N:54]([C:56]([C@@H:59]5[CH2:63][CH2:62][CH2:61][N:60]5[CH2:64][CH2:65][CH2:66][OH:67])=[N:57][N:58]=4)[CH:55]=3)[CH2:41][CH2:40]2)=[O:37])[N:26]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[N:27]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89623869HCID 89623869, compound

Product 1

HCID 89624255HCID 89624255, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF, 100 μL, 0.10 mmol) was added to a solution of Intermediate 84h (70.0 mg, 0.085 mmol) in THF (2.00 mL). The reaction was stirred for 2 h then partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-10% [2M NH3 in MeOH] in DCM. Further purification by HPLC (C18 X-select column, 10-98% MeCN in H2O, 0.1% HCO2H) gave the title compound as a white powder after freeze-drying (29 mg, 52%). LCMS (Method 5): Rt 3.63 min, m/z 663.3 [MH+]. 1H NMR (400 MHz, d4-MeOD): 1.30 (9H, s), 1.54-1.62 (2H, quin, J 7.0), 1.88-2.15 (6H, m), 2.20-2.37 (4H, m), 2.38 (3H, s), 2.55 (1H, dt, J 12.0, 8.1), 3.32-3.48 (3H, m), 4.11 (1H, t, J 8.0), 4.90 (1H, dd, J 9.1, 5.7), 5.31 (1H, t, J 4.0), 6.33 (1H, s), 7.20-7.36 (9H, m), 7.65 (1H, d, J 9.9), 8.32 (1H, d, J 1.7).

Workup

  1. customthen partitioned between EtOAc and water
  2. extractionThe aqueous layer was then extracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by FCC
  8. customFurther purification by HPLC (C18 X-select column, 10-98% MeCN in H2O, 0.1% HCO2H)

Sources & evidence

ORD record
ord-f5e8ae66dce34f2c9128e100a2544f89
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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