Potassium Hydroxide → HCID 44307090, compound

HRID 2210702Notes

Reaction equation

HRID 2210702 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][C@H:15]2[CH2:20][CH2:19][CH2:18][N:17]([CH2:21][C:22]([O:24]C)=[O:23])[C@H:16]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[K+]>O1CCCC1.O>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([CH2:13][O:14][C@H:15]2[CH2:20][CH2:19][CH2:18][N:17]([CH2:21][C:22]([OH:24])=[O:23])[C@H:16]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:4]=[C:3]([C:2]([F:32])([F:33])[F:1])[CH:8]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 10624372HCID 10624372, compound

Product 1

HCID 44307090HCID 44307090, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The methyl ester (1.8 g; Example 8) was dissolved in tetrahydrofuran (25 ml) and a solution of potassium hydroxide (0.6 g) in water (25 ml) was added. The reaction mixture was heated at reflux for 18 H, then the organic layer was removed in vacuo and the aqueous layer removed by freeze-drying. The residue was dissolved in the minimum volume of water and the pH adjusted to 7.0 by the addition of 2M hydrochloric acid. The precipitated solid was isolated by filtration and washed with water and then recrystallised from ethanol, m.p.=60°-63° C. Found: C, 53.11; H, 4.54; N, 3.05. Calcd. for C22H21F6NO3.HCl C, 53.08; H, 4.45; N, 2.81%. m/z (CI+) 462 (MH).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 H
  3. customthe organic layer was removed in vacuo
  4. customthe aqueous layer removed
  5. customby freeze-drying
  6. dissolutionThe residue was dissolved in the minimum volume of water
  7. additionthe pH adjusted to 7.0 by the addition of 2M hydrochloric acid
  8. customThe precipitated solid was isolated by filtration
  9. washwashed with water
  10. customrecrystallised from ethanol, m.p.=60°-63° C

Sources & evidence

ORD record
ord-e45a3b0c7a7c46aea525c0942304389e
Source dataset
uspto-grants-1995_10
Patent number
US05459270

Reaction notes

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