5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-(3-chloro-phenyl)-isoxazole-3-carboxylic acid ethylamide → [5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-(3-chloro-phenyl)-isoxazol-3-ylmethyl]-ethyl-amine

HRID 646480Notes

Reaction equation

HRID 646480 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)=[C:9]([C:18]2[CH:23]=[C:22]([Cl:24])[C:21]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:20][C:19]=2[O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:8][N:7]=1)=O)[CH3:2]>C1COCC1>[CH2:34]([O:33][C:19]1[CH:20]=[C:21]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:22]([Cl:24])=[CH:23][C:18]=1[C:9]1[O:8][N:7]=[C:6]([CH2:4][NH:3][CH2:1][CH3:2])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

3

Reactant 1

HCID 592647605-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-(3-chloro-phenyl)-isoxazole-3-carboxylic acid ethylamide

Product 1

HCID 59264726[5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-(3-chloro-phenyl)-isoxazol-3-ylmethyl]-ethyl-amineYield 68.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-(3-chloro-phenyl)-isoxazole-3-carboxylic acid ethylamide (36 mg, 0.06 mmol) in anhydrous THF under argon was added 1M Borane-THF complex (1 ml) and the solution refluxed overnight. After cooling the solution was poured on to a Isolute® SPE Flash SCX-2 5 g column which was quickly eluted with methanol (2×20 ml). The desired product was then recovered by eluting with a mixture of 10% ammonia in methanol (2×10 ml) which was evaporated in vaccuo to provide 23 mg (65% yield) of a light yellow powder.

Workup

  1. temperaturethe solution refluxed overnight
  2. temperatureAfter cooling the solution
  3. additionwas poured on to a Isolute® SPE Flash SCX-2 5 g column which
  4. washwas quickly eluted with methanol (2×20 ml)
  5. customThe desired product was then recovered
  6. washby eluting with a mixture of 10% ammonia in methanol (2×10 ml) which
  7. customwas evaporated in vaccuo

Sources & evidence

ORD record
ord-e1109152a772407da281e48ba26e3c7c
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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