Potassium Hydroxide → HCID 19049366, compound

HRID 742377Notes

Reaction equation

HRID 742377 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][CH2:15][CH:16]([NH:30][CH2:31][C:32]([O:34]C)=[O:33])[CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[K+]>O1CCCC1>[F:1][C:2]([F:36])([F:37])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][CH2:15][CH:16]([NH:30][CH2:31][C:32]([OH:34])=[O:33])[CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19049317HCID 19049317, compound

Product 1

HCID 19049366HCID 19049366, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-((3,5-bis (trifiuoromethyl)phenyl)methyloxy)-2-(N-((carbomethoxy) methyl)amino)-3,3-diphenylpropane (Example 1g, 2.38 g) in tetrahydrofuran (25 ml) was added 1M-potassium hydroxide solution (25 ml) and the mixture heated to reflux for 16 hours. The solvent was removed by evaporation and 1M-hydrochloric acid was added to an aqueous solution of the residue until pH=2. The gum which formed was recrystallised from aqueous ethanol to give N-(1-((3,5-bis(trifiuoromethyl) phenyl)methyloxy)-3,3- diphenylprop-2-yl)glycine mp 116°-119° C.; m/e (CI+) 512 (M+H), (CI-) 511 (M). Found: C, 60.06; H, 4.55; N, 2.66; C26H23NO3F6.0.5(H2O) requires C, 60.00; H, 4.64; N, 2.69%.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 16 hours
  3. customThe solvent was removed by evaporation and 1M-hydrochloric acid
  4. additionwas added to an aqueous solution of the residue until pH=2
  5. customThe gum which formed
  6. customwas recrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-131834fbf56d4415a6740218c39301be
Source dataset
uspto-grants-1996_09
Patent number
US05554633

Reaction notes

Loading…