Acetic Acid → 5-(2,4-bis(benzyloxy)-5-isopropylphenyl)-N-ethyl-4-(4-(morpholinomethyl)phenyl)isoxazole-3-carboxamide

HRID 1891178Notes

Reaction equation

HRID 1891178 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[C:10](I)=[C:9]([C:12]2[CH:17]=[C:16]([CH:18]([CH3:20])[CH3:19])[C:15]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:14][C:13]=2[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:8][N:7]=1)=[O:5])[CH3:2].[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.C([BH3-])#N.[Na+].[C:47](O)(=O)[CH3:48]>CO.C(Cl)Cl>[CH2:1]([NH:3][C:4]([C:6]1[C:10]([C:9]2[CH:12]=[CH:13][C:47]([CH2:48][N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[CH:6][CH:10]=2)=[C:9]([C:12]2[CH:17]=[C:16]([CH:18]([CH3:20])[CH3:19])[C:15]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:14][C:13]=2[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:8][N:7]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 247739595-(2,4-bis(benzyloxy)-5-isopropylphenyl)-N-ethyl-4-iodoisoxazole-3-carboxamide

Product 1

HCID 247736255-(2,4-bis(benzyloxy)-5-isopropylphenyl)-N-ethyl-4-(4-(morpholinomethyl)phenyl)isoxazole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

5-(2,4-Bis-benzyloxy-5-isopropyl-phenyl)-4-iodo-isoxazole-3-carboxylic acid ethylamide (1 eq) was dissolved in methanol and powdered 3A sieves were added. Morpholine (2 eq) was added, followed by sodium cyanoborohydride (2 eq). Acetic acid (5 eq) was added drop wise and the suspension was stirred under nitrogen at ambient temperature for 16 hours. The reaction mixture was diluted with DCM and washed with sat. NaHCO3(aq). The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The resulting gum was purified by flash chromatography, eluting with 1% MeOH in DCM to give 5-(2,4-Bis-benzyloxy-5-isopropyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide as a colourless oil.

Workup

  1. additionwere added
  2. washwashed with sat. NaHCO3(aq)
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting gum was purified by flash chromatography
  7. washeluting with 1% MeOH in DCM

Sources & evidence

ORD record
ord-80f1b0173c214167921c53077b2bdac2
Source dataset
uspto-grants-2013_08
Patent number
US08507480B2

Reaction notes

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