Citric Acid → HCID 67426433, compound

HRID 1516434Notes

Reaction equation

HRID 1516434 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[N:18]=[C:17]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[C:27]([I:28])[C:22]=4[N:21]=[N:20]3)[CH:16]=[CH:15][N:14]=2)[CH2:8][CH2:7]1)=[O:5])C.O[Li].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CCO.O>[I:28][C:27]1[C:22]2[N:21]=[N:20][N:19]([C:17]3[CH:16]=[CH:15][N:14]=[C:13]([NH:12][CH:9]4[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]4)[N:18]=3)[C:23]=2[CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 3

HCID 311Citric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67426454HCID 67426454, compound

Product 1

HCID 67426433HCID 67426433, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-[4-(4-iodobenzotriazol-1-yl)-pyrimidin-2-ylamino]-cyclohexane-carboxylic acid ethyl ester (2.56 g) in THF (20 mL), EtOH (20 mL) and H2O (15 mL) was added LiOH.H2O (0.65 g), and the resulting mixture stirred at RT overnight. The reaction mixture was then acidified with citric acid (2.99 g) in H2O (10 mL), and the solvent removed in vacuo. The resulting light orange solid was stirred in H2O for 30 min, filtered, washed with H2O, and dried to obtain 4-[4-(4-iodobenzotriazol-1-yl)-pyrimidin-2-ylamino]-cyclohexanecarboxylic acid (2.1 g, 87%) as a light orange powder. Mp=252-254° C.

Workup

  1. customthe solvent removed in vacuo
  2. stirringThe resulting light orange solid was stirred in H2O for 30 min
  3. filtrationfiltered
  4. washwashed with H2O
  5. customdried

Sources & evidence

ORD record
ord-9ba01894142e47aeb0f5b077ae3ceff7
Source dataset
uspto-grants-2012_07
Patent number
US08227478B2

Reaction notes

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