Tetrabutylammonium Fluoride → HCID 11813797, compound

HRID 2306213Notes

Reaction equation

HRID 2306213 reaction equation
[C:1]([O:5][C:6](=[O:59])[N:7]([C@H:25]1[CH2:29][CH2:28][N:27]([C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([O:40][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:38]=3)[CH:33]=[CH:32][CH:31]=2)[C:26]1=[O:58])[CH2:8][CH2:9][C:10]1[N:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[C:18]([F:24])[CH:17]=2)[CH:12]=[N:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][C:6](=[O:59])[N:7]([CH2:8][CH2:9][C:10]1[N:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[C:18]([F:24])[CH:17]=2)[CH:12]=[N:13][CH:14]=1)[C@H:25]1[CH2:29][CH2:28][N:27]([C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([OH:40])[CH:38]=3)[CH:33]=[CH:32][CH:31]=2)[C:26]1=[O:58])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 11767974HCID 11767974, compound

Product 1

HCID 11813797HCID 11813797, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-{1-[7-(tert-butyldiphenylsilyloxy)naphthalen-1-yl]-2-oxo-pyrrolidin-3-yl}-{2-[3-(4-cyano-3-fluorobenzyl)-3H-imidazol-4-yl]ethyl}carbamic acid tert-butyl ester, as described above in Step I, (500 mg, 0.619 mmol) in ThF (5 mL) was added TBAF (0.68 mL of a 1 M solution in THF, 0.68 mmol), dropwise. The mixture was stirred at ambient temperature for 30 min, then concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with CHCl3—2% MeOH—0.2% NH4OH to yield the desired phenol as a white foam.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash column chromatography on silica
  3. washeluting with CHCl3—2% MeOH—0.2% NH4OH

Sources & evidence

ORD record
ord-bc3e58a781a846b8973be87b2102126d
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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