Water → 3-[[2'-(1-Triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyloxy]-4-nitrobenzoic acid morpholide

HRID 2728Notes

Reaction equation

HRID 2728 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[C:11]([OH:13])=O.[H-].[Na+].[C:22]1([C:28]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[N:29]2[C:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]3[CH:45]=[CH:44][C:43]([CH2:46]Br)=[CH:42][CH:41]=3)=[N:32][N:31]=[N:30]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C)C=O>[C:54]1([C:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[N:29]2[C:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]3[CH:45]=[CH:44][C:43]([CH2:46][O:7][C:8]4[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=4[N+:17]([O-:19])=[O:18])[C:11]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:13])=[CH:42][CH:41]=3)=[N:32][N:31]=[N:30]2)[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 867523133-Hydroxy-4-nitrobenzoic acid morpholine

Product 1

HCID 867517083-[[2'-(1-Triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyloxy]-4-nitrobenzoic acid morpholideYield 101.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The compound ([3]-(32)-587) (0.99 g) prepared in Example 36 was dissolved in dry N,N-dimethylformamide (19 ml), and 50% sodium hydride (0.20 g) was added to the solution. The mixture was stirred at room temperature for 15 minutes. A solution of N-(triphenylmethyl)-5-[4'-(bromomethyl)biphenyl-2-yl]tetrazole (2.19 g) in N,N-dimethylformamide (6.5 ml) was added to the solution. The mixture was stirred at room temperature for 39 hours. The reaction mixture was added to water (50 ml), and extracted with chloroform (100 ml). The organic layer was washed, dried over anhydrous sodium sulfate, and concentrated to obtain the compound (2.72 g) as a light yellow solid. The product was purified by silica gel column chromatography (Kieselgel 60=190 g, chloroform/ethyl acetate=7/3) to obtain the compound ([3]-(33)-587) (1.41 g)

Workup

  1. stirringThe mixture was stirred at room temperature for 39 hours
  2. extractionextracted with chloroform (100 ml)
  3. washThe organic layer was washed
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d355d2b6749d4fb59a2aefb995bcd837
Source dataset
uspto-grants-1998_03
Patent number
US05731310

Reaction notes

Loading…