Ethyl 2-(diphenylmethyleneamino)acetate → HCID 86751784, compound

HRID 1957031Notes

Reaction equation

HRID 1957031 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH2:14]([O:16][C:17](=[O:33])[CH2:18][N:19]=[C:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:15]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[CH2:14]([O:16][C:17](=[O:33])[C@H:18]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[N:19]=[C:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH3:15]

Participants

6

Reactant 2

HCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 229975455-(4-(Bromomethyl)phenyl)isoxazole

Product 1

HCID 86751784HCID 86751784, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

5-(4-bromomethylphenyl)-isoxazole (700 mg) and N-diphenylmethylene-glycine ethyl ester (890 mg) are dissolved in dichloromethane (20 ml) and stirred vigorously with a solution of tetrabutylammonium hydrogensulfate in 2.5 molar aqueous sodium hydroxide, at room temperature, over night. The organic layer is then separated off and concentrated. The residue is partitioned between ether and water, the etherphase washed with water and brine, dried over magnesium sulfate and evaporated to give crude N-diphenylmethylene-3-[4-(5-isoxazolyl)-phenyl]-alanine ethyl ester, which is used for the next step without further purification.

Workup

  1. customThe organic layer is then separated off
  2. concentrationconcentrated
  3. customThe residue is partitioned between ether and water
  4. washthe etherphase washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-6825ea94f4344298990142f492cdf56c
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

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