Potassium Hydroxide → HCID 86690059, compound

HRID 539408Notes

Reaction equation

HRID 539408 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([C:17]2([C:33]([O:35]C)=[O:34])[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH2:19][CH2:18]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[CH2:26]([O:25][C:23]([N:20]1[CH2:19][CH2:18][C:17]([S:14]([C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:13][CH:12]=2)(=[O:16])=[O:15])([C:33]([OH:35])=[O:34])[CH2:22][CH2:21]1)=[O:24])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86690057HCID 86690057, compound

Product 1

HCID 86690059HCID 86690059, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

1-((Benzyloxy)carbonyl)-4-((4-phenoxyphenyl)sulfonyl)piperidine-4-carboxylic acid was synthesized as shown in FIG. 11. A 250 ml RBF was charged with the 1.75 g of 1-benzyl 4-methyl 4-((4-phenoxyphenyl)sulfonyl)piperidine-1,4-dicarboxylate (3.39 mmole), 0.57 g (10.16 mmole) potassium hydroxide in 30 ml ethanol/7.5 ml water. The reaction mixture was stirred at 50° C. with LCMS monitoring. LCMS analysis indicated ˜80% conversion after 1 hr and approximately 90% conversion after 2 hr with a trace of impurities appearing. The solution was concentrated to ¼ volume and partitioned between EA and 10% aq. Citric acid. The organics were washed with brine, dried, and concentrated in vacuo. The product was vacuum dried overnight to yield 1.6 g (95% yield) white solid that was used in Step 3.

Workup

  1. customafter 1 hr
  2. concentrationThe solution was concentrated
  3. custompartitioned between EA and 10% aq. Citric acid
  4. washThe organics were washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customdried overnight

Sources & evidence

ORD record
ord-c2d65abc41e6443bb719fb4287d93485
Source dataset
uspto-grants-2014_10
Patent number
US08871189B2

Reaction notes

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