HCID 1722082, compound → HCID 23134769, compound

HRID 2220146Notes

Reaction equation

HRID 2220146 reaction equation
[C:1]([NH:7][C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].CC(C)([O-])C.[K+].[C:25]1([C:31]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[N:32]2[N:36]=[C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[C:43]3[CH:48]=[CH:47][C:46]([CH2:49]Br)=[CH:45][CH:44]=3)[N:34]=[N:33]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(OCC)(=O)C.O>CN(C)C(=O)C>[C:57]1([C:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[N:32]2[N:36]=[C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[C:43]3[CH:48]=[CH:47][C:46]([CH2:49][N:7]([C:8]4[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=4)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5])=[CH:45][CH:44]=3)[N:34]=[N:33]2)[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Participants

6

Reactant 4

HCID 1722082HCID 1722082, compoundHCID 108646215-(4'-(Bromomethyl)-1,1'-biphenyl-2-yl)-2-triphenylmethyl-2H-tetrazoleHCID 22728543Water ethylacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 23134769HCID 23134769, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of ethyl 3-aminobenzoate (5.02 g) in N,N-dimethylacetamide (DMA, 50 ml) was added dropwise pentanoyl chloride (4.0 ml), and the mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogencarbonate was added to the reaction mixture, and the mixture was stirred for 1 hr. The mixture was partitioned and extracted by adding ethyl acetate, and the extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to give ethyl 3-(N-pentanoyl)aminobenzoate (7.55 g). To a solution of the obtained amide compound in DMA (100 ml) was added potassium tert-butoxide (4.09 g), and the mixture was stirred for 30 min. To the reaction mixture was added [4-[2-(3-triphenylmethyl-3H-tetrazol-5-yl)phenyl]phenyl]methylbromide (18.6 g), and the mixture was stirred at 50° C. for 3 hrs. The reaction mixture was added to ethyl acetate-water and, after partitioning and extraction, the extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluted with hexane-ethyl acetate:3-2 v/v) to give the object compound (20.6 g, yield 93.6%).

Workup

  1. stirringthe mixture was stirred at 50° C. for 3 hrs
  2. customafter partitioning
  3. extractionextraction
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (eluted with hexane-ethyl acetate:3-2 v/v)

Sources & evidence

ORD record
ord-d8a75957b6d94faaaf0ec5b8e2d9746e
Source dataset
uspto-grants-2008_08
Patent number
US07417052B2

Reaction notes

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