Diethyl Ether → HCID 178441886, compound

HRID 2259425Notes

Reaction equation

HRID 2259425 reaction equation
O=C(CCCC)C(CC1C=CC([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]2[N:25](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:24]=[N:23][N:22]=2)=CC=1)C(OC)=O.[K].O=[C:51]([CH2:57][CH2:58][CH2:59][CH3:60])[CH2:52][C:53](OC)=[O:54].[Br-].[Li+].BrCC1C=C[C:68]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)=[C:67]([C:77]2[N:81]([C:82](C3C=CC=CC=3)(C3C=CC=CC=3)[C:83]3C=C[CH:86]=[CH:85][CH:84]=3)N=N[N:78]=2)C=1.[CH3:101][CH2:102]OCC>CN(C)C=O>[CH2:83]([C:82]1[NH:81][C:77]([CH2:67][CH2:68][C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)=[N:78][C:53](=[O:54])[C:52]=1[CH2:51][C:57]1[CH:102]=[CH:101][C:60]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]2[NH:22][N:23]=[N:24][N:25]=2)=[CH:59][CH:58]=1)[CH2:84][CH2:85][CH3:86]

Participants

8

Reactant 6

HCID 3283Diethyl EtherHCID 82050Lithium BromideHCID 546075Methyl 3-oxoheptanoateHCID 5462222PotassiumHCID 10794130HCID 10794130, compoundHCID 189361215-[4-(Bromomethyl)[1,1′-biphenyl]-2-yl]-1-(triphenylmethyl)-1H-tetrazole

Product 1

HCID 178441886HCID 178441886, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

methyl 3-oxo-2-[[2'-(1-triphenylmethyl-1H-tetrazol-5yl)[1,1'-biphenyl]-4-yl]methyl]heptanoate. To a solution of 0.97 g of potassium 1,1-dimethylethylate in 15 ml of dimethylformamide, chilled on an ice bath, under an atmosphere of argon, a solution of 1.3 g of methyl 3-oxoheptanoate in 13 ml of dimethylformamide is added, followed by 1.67 g of lithium bromide and a solution of 5 g of 5-[4-(bromomethyl)[1,1'-biphenyl]-2-yl]-1-triphenylmethyl-1H-tetrazole in 25 ml of dimethylformamide. The reaction mixture is stirred for 5 hours at room temperature and then diluted with 300 ml of ether. The mixture is washed twice with 100 ml of water and then with 100 ml of a saturated aqueous solution of ammonium chloride. It is dried on magnesium sulfate and evaporated in vacuo to obtain 4.6 g of the product in the form of a yellow oil used as such in the following step.

Workup

  1. washThe mixture is washed twice with 100 ml of water
  2. customIt is dried on magnesium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-841dc951d2dc42d09fdb00334eaf7c5c
Source dataset
uspto-grants-1995_12
Patent number
US05472967

Reaction notes

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