Sodium Hydroxide → HCID 178489078, compound

HRID 2173946Notes

Reaction equation

HRID 2173946 reaction equation
[C:1]([C:3]1[CH:34]=[CH:33][C:6]2[NH:7][C:8]([C:10]([C:21]3[C:29]([O:30][CH3:31])=[CH:28][C:27]([CH3:32])=[C:26]4[C:22]=3[CH:23]=[CH:24][NH:25]4)([O:15][CH2:16][C:17]([O:19]C)=[O:18])[C:11]([F:14])([F:13])[F:12])=[N:9][C:5]=2[CH:4]=1)#[N:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([C:3]1[CH:34]=[CH:33][C:6]2[NH:7][C:8]([C:10]([C:21]3[C:29]([O:30][CH3:31])=[CH:28][C:27]([CH3:32])=[C:26]4[C:22]=3[CH:23]=[CH:24][NH:25]4)([O:15][CH2:16][C:17]([OH:19])=[O:18])[C:11]([F:13])([F:14])[F:12])=[N:9][C:5]=2[CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178501803HCID 178501803, compound

Product 1

HCID 178489078HCID 178489078, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

(+) or (−)-Methyl 2-(1-(5-cyano-1H-benzo[d]imidazol-2-yl)-2,2,2-trifluoro-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethoxy)acetate (tr=2.4 min—from Example 35-B) (116 mg, 0.246 mmol) was dissolved in THF (1.2 mL) and MeOH (1.2 mL). A 3N aq. NaOH solution (0.45 mL, 1.35 mmol) was added. The reaction was stirred at 40° C. for 1 hour. At this point the reaction mixture was concentrated. The residue was dissolved in MeOH, and purified with RP-HPLC(HC-A) to provide (−)-2-(1-(5-cyano-1H-benzo[d]imidazol-2-yl)-2,2,2-trifluoro-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethoxy)acetic acid.

Workup

  1. concentrationAt this point the reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in MeOH
  3. custompurified with RP-HPLC(HC-A)

Sources & evidence

ORD record
ord-c630e3044830457aaf6544e7f6d6744b
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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