Acetone → HCID 178430296, compound

HRID 1883508Notes

Reaction equation

HRID 1883508 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1)=[NH:4].[CH3:26][C:27]([CH3:29])=O>>[CH3:26][C:27]1([CH3:29])[O:1][N:2]=[C:3]([C:5]2[CH:6]=[CH:7][C:8]([CH2:11][CH:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:23])[F:25])[CH:17]=3)[C:13]([OH:15])=[O:14])=[CH:9][CH:10]=2)[NH:4]1

Participants

3

Reactant 2

HCID 180AcetoneHCID 178513294HCID 178513294, compound

Product 1

HCID 178430296HCID 178430296, compoundYield 40%

Procedure

A solution of 3-[4-(N-hydroxycarbamimidoyl)-phenyl]-2-(3-trifluoromethyl-phenyl)-propionic acid (200 mg, 0.57 mmol, example 258/259 b 1)) in acetone (50 ml) was refluxed for 8 hours per day for five days. The reaction mixture was evaporated in vacuo and the residue was purified by prep. HPLC (HPLC conditions: Purospher(R)Star HP-18e (10 μm), acetonitrile/water+1% TFA, 10% to 100% acetonitrile) to give 90 mg of the desired product (40%). MS m/z: 393.1 (M+H)+.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was purified by prep

Sources & evidence

ORD record
ord-4aae0b246aa7483d8961615fee03816b
Source dataset
uspto-grants-2004_07
Patent number
US06759420B1

Reaction notes

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