Sodium Hydroxide → (+)-3-(5-cyanobenzo[d]oxazol-2-yl)-3-(5-methoxy-7-methyl-1H-indol-4-yl)propanoic acid

HRID 2174120Notes

Reaction equation

HRID 2174120 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([C:17]3[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH3:28])=[C:22]4[C:18]=3[CH:19]=[CH:20][NH:21]4)[CH2:12][C:13]([O:15]C)=[O:14])=[N:8][C:7]=2[CH:29]=1)#[N:2].[OH-].[Na+]>C1COCC1.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([C:17]3[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH3:28])=[C:22]4[C:18]=3[CH:19]=[CH:20][NH:21]4)[CH2:12][C:13]([OH:15])=[O:14])=[N:8][C:7]=2[CH:29]=1)#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86701762(-)-methyl 3-(5-cyanobenzo[d]oxazol-2-yl)-3-(5-methoxy-7-methyl-1H-indol-4-yl)propanoate

Product 1

HCID 86701761(+)-3-(5-cyanobenzo[d]oxazol-2-yl)-3-(5-methoxy-7-methyl-1H-indol-4-yl)propanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To (+) or (−)-methyl 3-(5-cyanobenzo[d]oxazol-2-yl)-3-(5-methoxy-7-methyl-1H-indol-4-yl)propanoate (tr=3.8 min) (74 mg, 0.190 mmol) in THF (475 μl) and water (475 μl) was added NaOH (950 μl, 0.950 mmol) and the reaction stirred at room temperature for 4 hours. The reaction was directly purified via preparative HPLC (HC-B) to obtain the title compound. 1H NMR as in Example 148-B. HRMS calcd. for C21H17N3O4 (M+H)+ 376.1297. found 376.1290.

Workup

  1. customThe reaction was directly purified via preparative HPLC (HC-B)

Sources & evidence

ORD record
ord-a66d845cdf5a4e2797a33cc200cb8d0f
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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