Methanol → HCID 118290433, compound

HRID 628551Notes

Reaction equation

HRID 628551 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH3:37])[N:8]=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[C:25]([N:26]4[C:30](=[O:31])[N:29]([CH3:32])[N:28]=[N:27]4)=[CH:24][CH:23]=[CH:22][C:21]=3[CH:33]3[CH2:35][CH2:34]3)=[C:14]([CH3:36])[CH:13]=2)[C:10]=1[CH3:11])=[O:5])C.O1CCCC1.CO.[OH-].[Li+]>O>[CH:33]1([C:21]2[CH:22]=[CH:23][CH:24]=[C:25]([N:26]3[C:30](=[O:31])[N:29]([CH3:32])[N:28]=[N:27]3)[C:20]=2[CH2:19][O:18][C:15]2[CH:16]=[CH:17][C:12]([C:9]3[C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[N:7]([CH3:37])[N:8]=3)=[CH:13][C:14]=2[CH3:36])[CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 118290407HCID 118290407, compound2×

Product 1

HCID 118290433HCID 118290433, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At room temperature, the mixture of 5-{4-[2-Cyclopropyl-6-(4-methyl-5-oxo-4,5-dihydro-tetrazol-1-yl)-benzyloxy]-3-methyl-phenyl}-2,4-dimethyl-2H-pyrazole-3-carboxylic acid ethyl ester (Present compound 48) 1.4 g, tetrahydrofuran 40 ml, methanol 10 ml, water 10 ml and lithium hydroxide 0.2 g was stirred for twelve hours. The resulting mixture was concentrated under reduced pressure and was acidified with 10% hydrochloric acid solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and was dried over anhydrous magnesium sulfate, and was then concentrated under reduced pressure to give 5-{4-[2-Cyclopropyl-6-(4-methyl-5-oxo-4,5-dihydro-tetrazol-1-yl)-benzyloxy]-3-methyl-phenyl}-2,4-dimethyl-2H-pyrazole-3-carboxylic acid 1.3 g.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-78535b33bede427b95f9f6638eab5d92
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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