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Acetic Acid → 5-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide

HRID 646518
Notes
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Reaction equation

HRID 646518 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]=O)=[CH:13][CH:12]=2)=[C:9]([C:19]2[CH:24]=[C:23]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:22]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:21][C:20]=2[O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:8][N:7]=1)=[O:5])[CH3:2].[NH:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:1]([NH:3][C:4]([C:6]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([CH2:17][N:45]3[CH2:50][CH2:49][O:48][CH2:47][CH2:46]3)=[CH:15][CH:16]=2)=[C:9]([C:19]2[CH:24]=[C:23]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:22]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:21][C:20]=2[O:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[O:8][N:7]=1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 247735315-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-4-(4-formyl-phenyl)-isoxazole-3-carboxylic acid ethylamide

Product 1

HCID 247737085-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-4-(4-formyl-phenyl)-isoxazole-3-carboxylic acid ethylamide (1 eq) was dissolved in methanol and powdered 3 Å sieves were added. Morpholine (2 eq) was added, followed by acetic acid (5 eq). After stirring for 30 minutes, sodium cyanoborohydride (2 eq) was added portionwise and the suspension was stirred under nitrogen at ambient temperature for 16 hours. The reaction mixture was filtered through celite and concentrated to dryness. Column chromatography, eluting with 5% MeOH in DCM gave 5-(2,4-bis-benzyloxy-5-isobutyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide as a colourless oil.

Workup

  1. additionpowdered 3 Å sieves were added
  2. stirringthe suspension was stirred under nitrogen at ambient temperature for 16 hours
  3. filtrationThe reaction mixture was filtered through celite and
  4. concentrationconcentrated to dryness
  5. washColumn chromatography, eluting with 5% MeOH in DCM

Sources & evidence

ORD record
ord-ae9b8e2fb22f454a8e36dc78fab1e033
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07705027B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes