Benzyl Bromide → Methyl 8-(benzyloxy)-5-(5-(tert-butoxycarbonylamino)-N-methylpentyl-sulfonamido)-1,6-naphthyridine-7-carboxylate

HRID 455309Notes

Reaction equation

HRID 455309 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14]([N:17]([C:19]1[N:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[C:26]([OH:33])=[C:25]2[C:20]=1[CH:21]=[CH:22][CH:23]=[N:24]2)[CH3:18])(=[O:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:40](Br)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CN(C=O)C>[CH2:40]([O:33][C:26]1[C:27]([C:29]([O:31][CH3:32])=[O:30])=[N:28][C:19]([N:17]([CH3:18])[S:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])(=[O:16])=[O:15])=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[CH:21]2)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 67109690Methyl 5-(5-(tert-butoxycarbonylamino)-N-methylpentylsulfonamido)-8-hydroxy-1,6-naphthyridine-7-carboxylate

Product 1

HCID 67109489Methyl 8-(benzyloxy)-5-(5-(tert-butoxycarbonylamino)-N-methylpentyl-sulfonamido)-1,6-naphthyridine-7-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of methyl 5-(5-(tert-butoxycarbonylamino)-N-methylpentylsulfonamido)-8-hydroxy-1,6-naphthyridine-7-carboxylate (Example 2.2; 5.44 mmol), and Cs2CO3 (10.9 mmol) in DMF (11 ml) was added benzyl bromide (10.9 mmol). The mixture was stirred overnight. The crude mixture was extracted with AcOEt/water, dried over MgSO4 and concentrated. The product was purified by SiO2 column chromatography (1:1, AcOEt:Hex), to give the target compound in 75% yield.

Workup

  1. extractionThe crude mixture was extracted with AcOEt/water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe product was purified by SiO2 column chromatography (1:1, AcOEt:Hex)
  5. customto give the target compound in 75% yield

Sources & evidence

ORD record
ord-04bcba0516d24cefb98c59d335513630
Source dataset
uspto-grants-2013_07
Patent number
US08497270B2

Reaction notes

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