Tetrabutylammonium Fluoride → HCID 66997644, compound

HRID 18013Notes

Reaction equation

HRID 18013 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-8d03c26527ad4dbaadf53a89581e43cd
Source dataset
uspto-grants-2010_06
Patent number
US07741315B2

Reaction notes

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