Tetrabutylammonium Fluoride → HCID 60198394, compound

HRID 2279470Notes

Reaction equation

HRID 2279470 reaction equation
[Si]([O:8][C@H:9]([CH3:39])[C@@H:10]([NH:22][C:23]([N:25]1[CH2:34][CH2:33][C:32]2[CH:31]=[N:30][C:29]([NH:35][CH:36]([CH3:38])[CH3:37])=[N:28][C:27]=2[CH2:26]1)=[O:24])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[C:12]=1[F:21])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:21][C:12]1[C:13]([C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=[CH:16][C:11]=1[C@H:10]([NH:22][C:23]([N:25]1[CH2:34][CH2:33][C:32]2[CH:31]=[N:30][C:29]([NH:35][CH:36]([CH3:38])[CH3:37])=[N:28][C:27]=2[CH2:26]1)=[O:24])[C@@H:9]([OH:8])[CH3:39]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86705483HCID 86705483, compound

Product 1

HCID 60198394HCID 60198394, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 116 (533 mg, 0.936 mmol) and THF (10 mL) cooled to 0° C. was added TBAF (1.310 mL, 1.31 mmol) and reaction was stirred at RT for 45 min. The reaction was poured onto water and extracted with DCM. The organic layer was concentrated and the crude product was purified by SiO2 chromatography eluting with 1% MeOH/DCM to afford 269 mg (63.1%) of I-18: LCMS (ACPI-pos) m/z 420.3 (M+H)+.

Workup

  1. additionwas added
  2. additionThe reaction was poured onto water
  3. extractionextracted with DCM
  4. concentrationThe organic layer was concentrated
  5. customthe crude product was purified by SiO2 chromatography
  6. washeluting with 1% MeOH/DCM
  7. customto afford 269 mg (63.1%) of I-18

Sources & evidence

ORD record
ord-5508159a410f48e8a309c5e5ee07d374
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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