Hydrochloric Acid → (S)-2-sec-Butylamino-6-(2-methyl-2H-tetrazol-5-yl)-isonicotinic acid

HRID 732449Notes

Reaction equation

HRID 732449 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10]2[N:11]=[N:12][N:13]([CH3:15])[N:14]=2)[N:7]=[C:6]([NH:16][C@H:17]([CH2:19][CH3:20])[CH3:18])[CH:5]=1.[OH-].[Na+].Cl>CO>[C@@H:17]([NH:16][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([C:10]2[N:11]=[N:12][N:13]([CH3:15])[N:14]=2)[N:7]=1)[C:3]([OH:21])=[O:2])([CH2:19][CH3:20])[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68814453(S)-2-sec-Butylamino-6-(2-methyl-2H-tetrazol-5-yl)-isonicotinic acid methyl ester

Product 1

HCID 68816248(S)-2-sec-Butylamino-6-(2-methyl-2H-tetrazol-5-yl)-isonicotinic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Treat a solution of (S)-2-sec-butylamino-6-(2-methyl-2H-tetrazol-5-yl)-isonicotinic acid methyl ester (250 mg, 0.86 mmol) in methanol (5 mL) with 2 N NaOH (0.64 mL, 1.29 mmol). Stir at room temperature overnight, acidify the reaction to about pH=3 using 1 N HCl. Extract the reaction mixture with ethyl acetate (3×25 mL). Wash the combined organic layers with saturated aqueous sodium chloride, dry (sodium sulfate) and concentrate to give the title compound.

Workup

  1. customthe reaction to about pH=3
  2. extractionExtract the reaction mixture with ethyl acetate (3×25 mL)
  3. washWash the combined organic layers with saturated aqueous sodium chloride
  4. dry with materialdry (sodium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-a2f08d898c9e4441ab70a99c54d3a97b
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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