Toluene → 3-[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-ylamino]-propionic acid

HRID 348445Notes

Reaction equation

HRID 348445 reaction equation
C([O:5][C:6](=[O:26])[CH2:7][CH2:8][NH:9][C:10]1[N:15]=[CH:14][C:13]([C:16](=[O:25])[NH:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[CH:12][N:11]=1)(C)(C)C.C1(C)C=CC=CC=1>FC(F)(F)C(O)=O.O>[F:24][C:21]1[CH:20]=[CH:19][C:18]([NH:17][C:16]([C:13]2[CH:14]=[N:15][C:10]([NH:9][CH2:8][CH2:7][C:6]([OH:26])=[O:5])=[N:11][CH:12]=2)=[O:25])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 69522105HCID 69522105, compound

Product 1

HCID 160048053-[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-ylamino]-propionic acidYield 98%

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

A solution of 3-[5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylamino]propionic acid tert-butyl ester in 90% trifluoroacetic acid/water was stirred for 15 min. Toluene (4 mL) was added and the solution was concentrated in vacuo. A series of dilutions and concentrations were performed using acetic acid/toluene (1/1) followed by methanol/toluene (1/1). The resulting solids were triturated with ethyl acetate/hexane (2/1) to afford 61.1 mg (98% yield) of the titled product as a white solid. API-MS m/z 305 (MH)+, 303 (M−H)−.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. concentrationA series of dilutions and concentrations
  3. customThe resulting solids were triturated with ethyl acetate/hexane (2/1)

Sources & evidence

ORD record
ord-8c4d2270c1754a5aaf24056311d69ac5
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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