Sodium Hydroxide → HCID 59016038, compound

HRID 968862Notes

Reaction equation

HRID 968862 reaction equation
C([O:3][C:4](=[O:36])[C:5]([CH3:35])([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]2[N:20]([CH2:21][CH2:22][CH3:23])[C:19](=[O:24])[N:18]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[N:17]=2)=[CH:10][CH:9]=1)[CH3:6])C.[OH-].[Na+]>C(O)C>[CH3:6][C:5]([O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C:16]2[N:20]([CH2:21][CH2:22][CH3:23])[C:19](=[O:24])[N:18]([C:25]3[CH:26]=[CH:27][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:29][CH:30]=3)[N:17]=2)=[CH:12][CH:13]=1)([CH3:35])[C:4]([OH:36])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59016003HCID 59016003, compound

Product 1

HCID 59016038HCID 59016038, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methyl-2-(4-{2-[5-oxo-4-propyl-1-(4-trifluoromethyl-phenyl)-4,5-dihydro-1H-[1,2,4]triazol-3-yl]-ethyl}-phenoxy)-propionic acid ethyl ester (94 mg, 0.19 mmol) and a 2N solution of sodium hydroxide (2.3 mL) in ethanol (5 mL) was heated to 80° C. for 35 min. The solvent was evaporated, water added and the solution made acidic with concentrated hydrochloric acid (pH 0-1), extracted with ether. The combined organic extracts were washed with water, brine, dried and evaporated to dryness to afford the pure compound (82 mg, 92.3%): 1HNMR (400 MHz, CDCl3) δ 8.06 (d, 2H, J=8.3 Hz), 7.59 (d, 2H, J=8.3 Hz), 7.09 (d, 2H, 6.4 Hz), 6.83 (d, 2H, J=8.3 Hz), 3.45 (t, 2H, J=7.4 Hz), 3.02 (d, 2 H, J=7.3 Hz), 2.79 (m, 2H), 1.60 (m, 2H), 1.52 (s, 6H), 0.87 (t, 3H, J=7.8 Hz); ESMS m/z (relative intensity) 476.1 (M−H+, 50).

Workup

  1. customThe solvent was evaporated
  2. additionwater added
  3. extractionextracted with ether
  4. washThe combined organic extracts were washed with water, brine
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-70fa1b31f8ce49b39389c29b363aed95
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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