Tetrabutylammonium Fluoride → HCID 68294680, compound

HRID 2279477Notes

Reaction equation

HRID 2279477 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([NH:19][C:20]([N:22]1[CH2:31][CH:30]([OH:32])[C:29]2[CH:28]=[N:27][C:26]([NH:33][CH:34]([CH3:36])[CH3:35])=[N:25][C:24]=2[CH2:23]1)=[O:21])[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([Cl:18])[CH:12]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:18][C:13]1[CH:12]=[C:11]([C@H:10]([NH:19][C:20]([N:22]2[CH2:31][CH:30]([OH:32])[C:29]3[CH:28]=[N:27][C:26]([NH:33][CH:34]([CH3:36])[CH3:35])=[N:25][C:24]=3[CH2:23]2)=[O:21])[CH2:9][OH:8])[CH:16]=[CH:15][C:14]=1[F:17]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68294322HCID 68294322, compound

Product 1

HCID 68294680HCID 68294680, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 132 (35 mg, 0.0650 mmol) in THF (1 mL) cooled to 0° C. was added TBAF (91 μL, 0.0911 mmol) and reaction was stirred at RT for 2 h. The reaction was concentrated and the resulting residue was purified on a reverse phase column (SP4) eluting with a MeCN/H2O gradient (5 to 95% MeCN) to afford 17.2 mg (62.4%) of I-20: LCMS (ACPI-pos) m/z 424.1 (M+H)+.

Workup

  1. additionwas added
  2. concentrationThe reaction was concentrated
  3. customthe resulting residue was purified on a reverse phase column (SP4)
  4. washeluting with a MeCN/H2O gradient (5 to 95% MeCN)
  5. customto afford 17.2 mg (62.4%) of I-20

Sources & evidence

ORD record
ord-f783f7c97be044a694ef91c7d824c459
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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