Potassium Hydroxide → HCID 86690055, compound

HRID 539406Notes

Reaction equation

HRID 539406 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([C:17]3([C:30]([O:32]CC)=[O:31])[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH:2]=1.[OH-].[K+]>C(O)C.O>[C:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][C:17]([S:14]([C:11]2[CH:10]=[CH:9][C:8]([O:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:13][CH:12]=2)(=[O:15])=[O:16])([C:30]([OH:32])=[O:31])[CH2:18][CH2:19]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86690056HCID 86690056, compound

Product 1

HCID 86690055HCID 86690055, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

1-(tert-butoxycarbonyl)-4-(4-(pyridin-3-yloxy)phenylsulfonyl)piperidine-4-carboxylic acid was prepared according to FIG. 3. A 250-mL round bottom flask was charged with 1.7 g ethyl ester (from step 1), 0.78 g (4 eq.) potassium hydroxide in 16 mL ethanol and 4 mL water. The reaction mixture was heated to 90° C. LCMS after 1 hour shows complete reaction. The mixture was partitioned between ethyl acetate and 10% aqueous KHSO4-Brine. The yellow organic phase was separated, dried, filtered and concentrated. The residue was vacuum dried overnight to produce 1.32 g off-white foam that was used without further purification.

Workup

  1. customreaction
  2. customThe mixture was partitioned between ethyl acetate and 10% aqueous KHSO4-Brine
  3. customThe yellow organic phase was separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried overnight

Sources & evidence

ORD record
ord-1f37aae45a514cffb79f72c56162539e
Source dataset
uspto-grants-2014_10
Patent number
US08871189B2

Reaction notes

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