Hydrofluoric Acid → HCID 59736761, compound

HRID 252814Notes

Reaction equation

HRID 252814 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH2:7][C:8]#[C:9][C:10]1[CH:11]=[CH:12][C:13]([N+:37]([O-:39])=[O:38])=[C:14]([NH:16][C:17](=[O:36])[C:18]2[CH:23]=[CH:22][C:21]([CH2:24][NH:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=3)=[CH:20][CH:19]=2)[CH:15]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.F>C1COCC1.N1C=CC=CC=1.C(OCC)(=O)C>[CH3:35][O:34][C:28]1[CH:27]=[C:26]([NH:25][CH2:24][C:21]2[CH:22]=[CH:23][C:18]([C:17]([NH:16][C:14]3[CH:15]=[C:10]([C:9]#[C:8][CH2:7][OH:6])[CH:11]=[CH:12][C:13]=3[N+:37]([O-:39])=[O:38])=[O:36])=[CH:19][CH:20]=2)[CH:31]=[CH:30][C:29]=1[O:32][CH3:33]

Participants

7

Reactant 3

HCID 14917Hydrofluoric AcidHCID 2724141Tetrabutylammonium FluorideHCID 59736816HCID 59736816, compound

Product 1

HCID 59736761HCID 59736761, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of compound 74 (871 mg, 1.24 mmol) in THF (3 mL) was treated with 1.0 M solution of tetrabutylammonium fluoride in THF (2.0 mL, 2.0 mmol) followed by 70% hydrogen fluoride in pyridine (0.1 mL), and the solution stirred under nitrogen for 12 h, diluted with ethyl acetate (200 mL) and washed with saturated NaHCO3 (50 mL) and then with water (6×100 mL), dried (Na2SO4), filtered and concentrated in vacuum. The crude material (647 mg) was pure enough for the next step without further purification.

Workup

  1. washwashed with saturated NaHCO3 (50 mL)
  2. dry with materialwith water (6×100 mL), dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customThe crude material (647 mg) was pure enough for the next step without further purification

Sources & evidence

ORD record
ord-ec677a374fef43eb874ec5ebeda74047
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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