3-Phenylbutanal → 1-{4'-[3-Methyl-4-(3-phenyl-butylamino)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid

HRID 1528707Notes

Reaction equation

HRID 1528707 reaction equation
C([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[NH2:27])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])C.[C:28]1([CH:34]([CH3:38])[CH2:35][CH:36]=O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O.[OH-].[Li+]>C(Cl)Cl.CO.O>[CH3:26][C:23]1[C:22]([NH:27][CH2:36][CH2:35][CH:34]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH3:38])=[C:21]([C:18]2[CH:17]=[CH:16][C:15]([C:12]3[CH:13]=[CH:14][C:9]([C:6]4([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]4)=[CH:10][CH:11]=3)=[CH:20][CH:19]=2)[O:25][N:24]=1

Participants

7

Reactant 4

HCID 859793-PhenylbutanalHCID 168937Lithium hydroxide, monohydrateHCID 5049666Sodium triacetoxyborohydrideHCID 665771951-[4'-(4-Amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 513523001-{4'-[3-Methyl-4-(3-phenyl-butylamino)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

1-[4′-(4-Amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.1 g, 0.27 mmol), 3-phenyl-butyraldehyde (0.048 g, 0.33 mmol) and sodium triacetoxyborohydride (0.11 g, 0.54 mmol) were mixed in CH2Cl2 and stirred overnight. Lithium hydroxide monohydrate (0.100 g, 2.38 mmol) in MeOH/H2O was added and the reaction stirred at 60° C. for 1 hour. The reaction was submitted to standard aqueous workup to yield the title compound.

Workup

  1. stirringthe reaction stirred at 60° C. for 1 hour

Sources & evidence

ORD record
ord-58902418e25c4c219b5b3457d9663e38
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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