Tetramethylammonium Hydroxide Pentahydrate → (+/-)-alpha-tert.Butyloxycarbonylamino-3-(4'-chloro-5-(diethoxyphosphinyl)methyl-[1.1'-biphenyl]-3-yl) propanoic acid cinnamyl ester

HRID 1109453

Reaction equation

HRID 1109453 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[CH:15]=[C:16]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[CH:17]=[C:18]([CH2:20][P:21]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])=[O:22])[CH:19]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O.O.O.O.[OH-].C[N+](C)(C)C.[CH2:47](Br)[CH:48]=[CH:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>CN(C)C=O>[CH2:47]([O:11][C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:13][C:14]1[CH:15]=[C:16]([C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)[CH:17]=[C:18]([CH2:20][P:21]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])=[O:22])[CH:19]=1)[CH:48]=[CH:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

5

Reactant 3

HCID 82620Tetramethylammonium Hydroxide PentahydrateHCID 98116BromomethylstyreneHCID 14127515HCID 14127515, compound

Product 1

HCID 56990101(+/-)-alpha-tert.Butyloxycarbonylamino-3-(4'-chloro-5-(diethoxyphosphinyl)methyl-[1.1'-biphenyl]-3-yl) propanoic acid cinnamyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.05 g of the product of step b) in 5 ml dimethylformamide are added 362 mg tetramethyl ammonium hydroxide pentahydrate. The mixture is stirred at room temperature 11/2 hours and then treated with 394 mg cinnamyl bromide. The mixture is stirred at room temperature 17 hours. The mixture is diluted with ice/water (about 50 ml) and extracted with diethyl ether. The extracts are washed with 10 ml aqueous 1N KHCO3 solution, dried (Na2SO4) and evaporated to give the heading compound as an oil.

Workup

  1. stirringThe mixture is stirred at room temperature 17 hours
  2. extractionextracted with diethyl ether
  3. washThe extracts are washed with 10 ml aqueous 1N KHCO3 solution
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-03ee18f2704e47f690db436e7429b7f1
Source dataset
uspto-grants-1994_06
Patent number
US05321016

Linked notes

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