1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → HCID 178485559, compound

HRID 480455Notes

Reaction equation

HRID 480455 reaction equation
BrC1C=C2C(=CC=1)C(C(NC)=O)=C(O[Si](C(C)(C)C)(C)C)C=C2.CC(C)C(C1N=CN(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=1)O.[Si]([O:60][C:61]1[CH:70]=[CH:69][C:68]2[C:63](=[CH:64][CH:65]=[C:66]([C:71]([OH:99])([C:75]3[N:76]=[CH:77][N:78](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:79]=3)[CH:72]([CH3:74])[CH3:73])[CH:67]=2)[C:62]=1[C:100]([NH:102][CH3:103])=[O:101])(C(C)(C)C)(C)C.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:60][C:61]1[CH:70]=[CH:69][C:68]2[C:63](=[CH:64][CH:65]=[C:66]([C:71]([OH:99])([C:75]3[N:76]=[CH:77][NH:78][CH:79]=3)[CH:72]([CH3:74])[CH3:73])[CH:67]=2)[C:62]=1[C:100]([NH:102][CH3:103])=[O:101]

Participants

6

Reactant 4

HCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 187690182-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanolHCID 187690492-(tert-butyldimethylsilyloxy)-6-[1-hydroxy-2-methyl-1-(-1-trityl-1H-imidazol-4-yl)propyl]-N-methyl-1-naphthamideHCID 187691556-Bromo-2-(tert-butyldimethylsilyloxy)-N-methyl-1-naphthamide

Product 1

HCID 178485559HCID 178485559, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Bromo-2-(tert-butyldimethylsilyloxy)-N-methyl-1-naphthamide (3.30 g) and 2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (2.66 g) were used as the starting materials. By the same procedure described in Reference example 33-(i), a crude mixture of 2-(tert-butyldimethylsilyloxy)-6-[1-hydroxy-2-methyl-1-(-1-trityl-1H-imidazol-4-yl)propyl]-N-methyl-1-naphthamide was obtained. The crude mixture and tetrabutylammonium fluoride hydrate (3.00 g) was dissolved in THF (30 mL), and the solution was stirred for 1 h at room temperature. After dilution with water, the resulting mixture was extracted with AcOEt. The organic layer was washed with brine and dried over MgSO4 followed by concentrating in vacuo. The residue was purified by flash column chromatography on silica gel (hexane:AcOEt=2:1→1:2) to give a colorless solid. The solid was washed with iPr2O to afford the titled compound (1.48 g) as a colorless powder.

Workup

  1. customwas obtained
  2. extractionAfter dilution with water, the resulting mixture was extracted with AcOEt
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationby concentrating in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (hexane:AcOEt=2:1→1:2)
  7. customto give a colorless solid
  8. washThe solid was washed with iPr2O

Sources & evidence

ORD record
ord-889107be2c4b495f855027a39f53a839
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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