Water → HCID 68156267, compound

HRID 1892739Notes

Reaction equation

HRID 1892739 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:26]=[C:27]([CH3:38])[C:28]=1[N:29]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[N:30]1)[O:5][CH:6]([C:10]1[CH:25]=[CH:24][C:13]([C:14]([NH:16][CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[O:15])=[CH:12][CH:11]=1)[CH2:7][CH2:8][CH3:9].O.O1CCCC1.O.[OH-].[Li+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH:26]=[C:27]([CH3:38])[C:28]=1[N:29]1[CH:33]=[C:32]([C:34]([F:36])([F:35])[F:37])[CH:31]=[N:30]1)[O:5][CH:6]([C:10]1[CH:11]=[CH:12][C:13]([C:14]([NH:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[O:15])=[CH:24][CH:25]=1)[CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68157481HCID 68157481, compound

Product 1

HCID 68156267HCID 68156267, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a flask containing ethyl 3-(4-(1-(3,5-dimethyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzamido)propanoate (117 mg, 0.22 mmol) was added water (0.55 mL), tetrahydrofuran (0.55 mL), and methanol (0.55 mL). Lithium hydroxide monohydrate (508 mg, 12.1 mmol) was then added. The suspension was stirred at room temperature for 18 hours. The reaction was concentrated and acidified to pH=3 with citric acid (10%). A white precipitate formed. The solid was filtered, rinsed with water, and dried under vacuum to give (+/−)-3-(4-(1-(3,5-dimethyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzamido)propanoic acid (90 mg, 81%) as a white solid. 1H NMR (400 MHz, CDCl3, δ): 7.88 (s, 1H), 7.73 (d, J=8.2 Hz, 2H), 7.65 (s, 1H), 7.39 (d, J=8.4 Hz, 2H), 6.80 (t, J=5.9 Hz, 1H), 6.56 (s, 2H), 5.16 (dd, J=7.8, 5.1 Hz, 1H), 3.71 (q, J=5.9 Hz, 2H), 2.69 (t, J=5.8 Hz, 2H), 2.04-1.91 (m, 1H), 1.88 (s, 6H), 1.86-1.67 (m, 1H), 1.63-1.31 (m, 2H), 0.96 (t, J=7.3 Hz, 3H). MS (M+1): 504.

Workup

  1. concentrationThe reaction was concentrated
  2. customA white precipitate formed
  3. filtrationThe solid was filtered
  4. washrinsed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-4c22533c9fa4464797abb75f74754283
Source dataset
uspto-grants-2013_08
Patent number
US08507533B2

Reaction notes

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