HCID 58031819, compound → HCID 56602328, compound

HRID 240256Notes

Reaction equation

HRID 240256 reaction equation
[Br:1][C:2]1[CH:31]=[CH:30][C:5]([O:6][C:7]([CH3:29])([CH3:28])[C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH:21](C(O)=O)[C:22]([OH:24])=[O:23])[C:18]#[C:19][CH3:20])=[CH:13][CH:12]=2)=[O:9])=[C:4]([Cl:32])[CH:3]=1>O1CCOCC1>[Br:1][C:2]1[CH:31]=[CH:30][C:5]([O:6][C:7]([CH3:28])([CH3:29])[C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([CH:17]([C:18]#[C:19][CH3:20])[CH2:21][C:22]([OH:24])=[O:23])=[CH:15][CH:16]=2)=[O:9])=[C:4]([Cl:32])[CH:3]=1

Participants

3

Reactant 1

HCID 58031819HCID 58031819, compound

Product 1

HCID 56602328HCID 56602328, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 171 mg of 2-(1-{4-[2-(4-bromo-2-chlorophenoxy)-2-methylpropionylamino]phenyl}but-2-ynyl)malonic acid in 5 ml of dioxane was boiled at 120° C. for 17 h. The reaction mixture was concentrated and separated by means of preparative HPLC (Merck Hibar Purospher Star RP-18e 10 μm 25×250 mm; A: H2O+0.05% TFA; B: ACN+0.05% TFA; flow rate: 50 ml/min; in 15 minutes 10% B→90% B). The product fractions were freeze-dried to obtain 85 mg (54%) of 3-{4-[2-(4-bromo-2-chlorophenoxy)-2-methylpropionylamino]phenyl}hex-4-ynoic acid. C22H21BrClNO4 (478.77), LCMS (ESI-pos): 478/480/482 (M+H+).

Workup

  1. customfor 17 h
  2. concentrationThe reaction mixture was concentrated
  3. customseparated by means of preparative HPLC (Merck Hibar Purospher Star RP-18e 10 μm 25×250 mm
  4. customThe product fractions were freeze-dried

Sources & evidence

ORD record
ord-cdd9a7e994a24d54a3c9a170e33964f3
Source dataset
uspto-grants-2014_02
Patent number
US08648038B2

Reaction notes

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