Acetyl chloride → 4-Acetylamino-5-(2,4-bis-benzyloxy-5-chloro-phenyl)-isoxazole-3-carboxylic acid ethylamide

HRID 389930Notes

Reaction equation

HRID 389930 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([O:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([Cl:27])=[CH:15][C:14]=1[C:28]1[O:32][N:31]=[C:30]([C:33]([NH:35][CH2:36][CH3:37])=[O:34])[C:29]=1[NH2:38])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)Cl>[CH2:36]([NH:35][C:33]([C:30]1[C:29]([NH:38][C:1](=[O:3])[CH3:2])=[C:28]([C:14]2[CH:15]=[C:16]([Cl:27])[C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:18][C:13]=2[O:12][CH2:5][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:32][N:31]=1)=[O:34])[CH3:37]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 569268115-[2,4-bis(benzyloxy)-5-chlorophenyl]-4-amino-N-ethylisoxazole-3-carboxamide

Product 1

HCID 670833824-Acetylamino-5-(2,4-bis-benzyloxy-5-chloro-phenyl)-isoxazole-3-carboxylic acid ethylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of acetyl chloride (1.45 mmol) in DCM were added 5-[2,4-bis(benzyloxy)-5-chlorophenyl]-4-amino-N-ethylisoxazole-3-carboxamide (1.45 mmol, 700 mg) and TEA (1.74 mmol, 0.24 ml) dropwise. The mixture was stirred for 5 h, diluted with DCM and washed HCl 1N. The organic extract was dried and filtered. Solvents were removed under vacuo to give the crude residue that was purified by flash chromatography on silica gel.

Workup

  1. washwashed HCl 1N
  2. extractionThe organic extract
  3. customwas dried
  4. filtrationfiltered
  5. customSolvents were removed under vacuo

Sources & evidence

ORD record
ord-abf54c071e52406c8c06469613a48c2b
Source dataset
uspto-grants-2013_02
Patent number
US08383616B2

Reaction notes

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