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

HRID 646519Notes

Reaction equation

HRID 646519 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-2a17fd268d7449e5bb350c23bfdf1856
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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