Potassium Hydroxide → HCID 87998656, compound

HRID 895348Notes

Reaction equation

HRID 895348 reaction equation
C[O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([N:28]2[CH2:33][CH2:32][N:31]([CH2:34][C:35]([O:37]C)=[O:36])[CH2:30][CH2:29]2)[CH2:11][O:12][CH2:13][C:14]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=2)=[CH:6][CH:5]=1.[OH-].[K+]>CO>[OH2:2].[F:27][C:24]([F:25])([F:26])[C:16]1[CH:15]=[C:14]([CH:19]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:17]=1)[CH2:13][O:12][CH2:11][CH:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:39])=[O:2])=[CH:5][CH:6]=1)[N:28]1[CH2:29][CH2:30][N:31]([CH2:34][C:35]([OH:37])=[O:36])[CH2:32][CH2:33]1.[F:27][C:24]([C:16]1[CH:15]=[C:14]([CH:19]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:17]=1)[CH2:13][O:12][CH2:11][CH:10]([C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:39])=[O:2])=[CH:9][CH:8]=1)[N:28]1[CH2:33][CH2:32][N:31]([CH2:34][C:35]([OH:37])=[O:36])[CH2:30][CH2:29]1)([F:26])[F:25]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86590286HCID 86590286, compound2×

Product 1

HCID 87998656HCID 87998656, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In a round-bottomed flask were introduced 4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-(4-methoxycarbonylmethyl-piperazin-1-yl)-ethyl]-benzoic acid methyl ester (compound 316 prepared at example 2; 2 g, 3.56 mmoles), KOH (0.4 g, 7.12 mmoles) and MeOH. The reaction mixture was heated at 60° C. for 6 hours. MeOH was removed under reduce pressure and the residue was taken up by water. The pH was adjusted to 3-4 and the solution was extracted with AcOEt. The organic combined layers were dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel (eluent: CH2Cl2/MeOH/H2O: 90/10/1 v/v/v) to give 4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-(4-carboxymethyl-piperazin-1-yl)-ethyl]-benzoic acid hemihydrate (compound 319; 0.88 g, 45%).

Workup

  1. customMeOH was removed
  2. extractionthe solution was extracted with AcOEt
  3. dry with materialThe organic combined layers were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (eluent: CH2Cl2/MeOH/H2O: 90/10/1 v/v/v)

Sources & evidence

ORD record
ord-8d3acf2f291543388a84694545f014cf
Source dataset
uspto-grants-2005_07
Patent number
US06916797B2

Reaction notes

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