HCID 58031810, compound → HCID 56602329, compound

HRID 240259Notes

Reaction equation

HRID 240259 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:31]=[CH:32][CH:33]=1)[O:8][CH:9]([CH3:30])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH:23](C(O)=O)[C:24]([OH:26])=[O:25])[C:20]#[C:21][CH3:22])=[CH:15][CH:14]=1)=[O:11])([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1>[C:1]([C:5]1[CH:6]=[C:7]([CH:31]=[CH:32][CH:33]=1)[O:8][CH:9]([CH3:30])[C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]([C:20]#[C:21][CH3:22])[CH2:23][C:24]([OH:26])=[O:25])=[CH:17][CH:18]=1)=[O:11])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 58031810HCID 58031810, compound

Product 1

HCID 56602329HCID 56602329, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 304 mg (0.67 mmol) of 2-(1-{4-[2-(3-tert-butylphenoxy)propionylamino]-phenyl}but-2-ynyl)malonic acid in 10 ml of dioxane was boiled at 120° C. for 27 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 10 minutes 10% B→80% B; in 5 minutes 80% B→90% B). The product fractions were freeze-dried to obtain 214 mg (78%) of 3-{4-[2-(3-tert-butylphenoxy)propionylamino]phenyl}hex-4-ynoic acid. C25H29NO4 (407.51), LCMS (ESI-pos): 408 (M+H+).

Workup

  1. customfor 27 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. waitin 5 minutes 80% B→90% B)
  5. customThe product fractions were freeze-dried

Sources & evidence

ORD record
ord-4fea6039c1fc45a4920142ba78834af7
Source dataset
uspto-grants-2014_02
Patent number
US08648038B2

Reaction notes

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