Water → HCID 68156267, compound

HRID 537522Notes

Reaction equation

HRID 537522 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-761b31d4fdbd45e1bce5aa64a3661123
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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