Tetrabutylammonium Fluoride → HCID 66997644, compound

HRID 2066595Notes

Reaction equation

HRID 2066595 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][N:11]([CH2:37][CH2:38][CH2:39][CH2:40][O:41][Si](C(C)(C)C)(C)C)[C:12]([C:14]1[NH:15][C:16](=[O:36])[C:17]([O:34][CH3:35])=[C:18]2[C:23]=1[CH2:22][CH2:21][N:20]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[C:27]([Cl:32])[CH:26]=1)[C:19]2=[O:33])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:8][CH2:9][CH2:10][N:11]([CH2:37][CH2:38][CH2:39][CH2:40][OH:41])[C:12]([C:14]1[NH:15][C:16](=[O:36])[C:17]([O:34][CH3:35])=[C:18]2[C:23]=1[CH2:22][CH2:21][N:20]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[C:27]([Cl:32])[CH:26]=1)[C:19]2=[O:33])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66996905N-[2-(Benzyloxy)ethyl]-N-(4-{[tert-butyl(dimethyl)silyl]oxy}butyl)-6-(3-chloro-4-fluorobenzyl)-4-methoxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide

Product 1

HCID 66997644HCID 66997644, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-[2-(benzyloxy)ethyl]-N-(4-{[tert-butyl(dimethyl)silyl]-oxy}butyl)-6-(3-chloro-4-fluorobenzyl)-4-methoxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide (0.41 g, 0.59 mmol) in THF, a solution of tetra-n-butyl-ammonium fluoride (0.65 mL, 1M) in THF was added. The reaction mixture was stirred at room temperature overnight, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 3% methanol in dichloromethane. Collection and concentration of appropriate fractions afforded the title compound.

Workup

  1. concentrationconcentrated under vacuum
  2. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-48decc00a77f4fb9b100f46b91cce0df
Source dataset
uspto-grants-2012_10
Patent number
US08293731B2

Reaction notes

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