Sodium Hydroxide → HCID 178424315, compound

HRID 632947Notes

Reaction equation

HRID 632947 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:43])[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:42])[CH2:21][CH2:22][NH:23][C:24]([C:26]3[C:27]([C:38]([F:41])([F:40])[F:39])=[N:28][N:29]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[CH3:37])[CH:30]=3)=O)=[CH:15][CH:14]=2)[CH2:9][CH2:8]1>C1COCC1.CO.O>[C:32]1([CH3:37])[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[N:29]1[CH:30]=[C:26]([CH2:24][NH:23][CH2:22][CH2:21][C:20]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([C@H:10]3[CH2:9][CH2:8][C@H:7]([CH2:6][C:5]([OH:43])=[O:4])[CH2:12][CH2:11]3)=[CH:14][CH:15]=2)=[O:42])[C:27]([C:38]([F:41])([F:39])[F:40])=[N:28]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178500670HCID 178500670, compound

Product 1

HCID 178424315HCID 178424315, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
25 °C

Procedure

NaOH (52.6 mg, 1.3 mmol) was added to trans-[4-(4-{3-[(1-o-tolyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl)amino]propionylamino}phenyl)cyclohexyl]acetic acid methyl ester (75 mg, 0.13 mmol) dissolved in THF/MeOH/water (20 mL, 3:2:1). The reaction mixture was stirred at 25° C. for 5 hours and concentrated under vacuum. The residue was acidified with 1M HCl up to pH of 2 and extracted with ethyl acetate. The extract was washed with brine and dried with anhydrous sodium sulfate and concentrated under vacuum. The residue was stirred with acetonitrile and filtered. The filtrate was eluted with a gradient of methanol/DCM (5-10%) on a silica gel by column chromatography and purified. Accordingly, the desired compound (70 mg, 96%) was obtained as a white solid.

Workup

  1. concentrationconcentrated under vacuum
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. stirringThe residue was stirred with acetonitrile
  7. filtrationfiltered
  8. washThe filtrate was eluted with a gradient of methanol/DCM (5-10%) on a silica gel by column chromatography
  9. custompurified

Sources & evidence

ORD record
ord-d2449f658b9d424a857404394095a136
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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