Dichloromethane → 5-[2,4-dihydroxy-5-(2-methylpropyl)phenyl]-N-ethyl-4-[4-(morpholin-4-ylmethyl)phenyl]-1,2-oxazole-3-carboxamide

HRID 2097305Notes

Reaction equation

HRID 2097305 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:13][CH:12]=2)=[C:9]([C:24]2[CH:29]=[C:28]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:27]([O:34]CC3C=CC=CC=3)=[CH:26][C:25]=2[O:42]CC2C=CC=CC=2)[O:8][N:7]=1)=[O:5])[CH3:2].C(Cl)Cl.B(Cl)(Cl)Cl>CO>[CH2:1]([NH:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:13][CH:12]=2)=[C:9]([C:24]2[CH:29]=[C:28]([CH2:30][CH:31]([CH3:32])[CH3:33])[C:27]([OH:34])=[CH:26][C:25]=2[OH:42])[O:8][N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 25135Boron TrichlorideHCID 247737085-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide

Product 1

HCID 1354856345-[2,4-dihydroxy-5-(2-methylpropyl)phenyl]-N-ethyl-4-[4-(morpholin-4-ylmethyl)phenyl]-1,2-oxazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide (1 eq) was dissolved in an. DCM and under a nitrogen atmosphere, was cooled to 0° C. 1M BCl3 in DCM (9 eq) was added dropwise and the solution was stirred for 30 minutes. Methanol (2 ml) was added and the reaction mixture was concentrated in vacuo. Purification of the sample by preparative LC/MS gave 5-(2,4-dihydroxy-5-isobutyl-phenyl)-4-(4-morpholin-4-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customPurification of the sample by preparative LC/MS

Sources & evidence

ORD record
ord-0cb2e9ab768c48faa78f3fa7cd9a6805
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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