Tetrabutylammonium Fluoride → HCID 67497468, compound

HRID 1628264Notes

Reaction equation

HRID 1628264 reaction equation
[Si]([O:18][CH2:19][CH2:20][N:21]1[C:25]([NH:26][C:27](=[O:44])[C@@H:28]([NH:37][CH2:38][C:39]2[N:40]=[CH:41][S:42][CH:43]=2)[CH2:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[CH:24][C:23]([C:45]2[CH:50]=[CH:49][N:48]=[C:47]([NH:51][CH3:52])[CH:46]=2)=[N:22]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:29][C@H:28]([NH:37][CH2:38][C:39]2[N:40]=[CH:41][S:42][CH:43]=2)[C:27]([NH:26][C:25]2[N:21]([CH2:20][CH2:19][OH:18])[N:22]=[C:23]([C:45]3[CH:50]=[CH:49][N:48]=[C:47]([NH:51][CH3:52])[CH:46]=3)[CH:24]=2)=[O:44])=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67496689HCID 67496689, compound

Product 1

HCID 67497468HCID 67497468, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a flask with 30.C (110 mg, 0.15 mmol) was added THF 1.2 mL, and 0.2 mL TBAF (1M, 0.3 mmol). After 2 hours, the reaction was concentrated and worked up with water and 30% isopropanol in chloroform. The organic phase was washed with water and brine, dried and concentrated. Reverse phase HPLC purification 5-40% afforded product 30 (32 mg, 43%). 1H NMR (400 MHz, MeOH) δ ppm 8.93 (d, J=1.96 Hz, 1H) 7.94 (d, J=5.48 Hz, 1H) 7.39 (d, J=1.96 Hz, 1H) 7.23 (dd, J=8.61, 5.48 Hz, 2H) 6.98-7.05 (m, 2H) 6.93-6.97 (m, 1H) 6.89 (s, 1H) 6.76 (s, 1H) 4.12 (td, J=5.09, 1.96 Hz, 2H) 3.84-4.01 (m, 4H) 3.57 (dd, J=7.82, 5.87 Hz, 1H) 3.10 (dd, J=13.69, 7.80 Hz, 1H) 2.95 (dd, J=13.69, 7.83 Hz, 1H) 2.91 (s, 3H).

Workup

  1. concentrationthe reaction was concentrated
  2. washThe organic phase was washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. customReverse phase HPLC purification 5-40%

Sources & evidence

ORD record
ord-7c18c4513b124415a1252f856ba5df91
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

Loading…