Methanol → HCID 67217792, compound

HRID 1505283Notes

Reaction equation

HRID 1505283 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:28])=[N:8][N:9]([C:11]2[CH2:15][C:14]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=2)[CH:10]=1)=[O:5])C.[OH-].[Na+].CO>C1COCC1.O>[Cl:26][C:24]1[CH:25]=[C:20]([C:14]2([C:16]([F:18])([F:17])[F:19])[O:13][N:12]=[C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[C:7]([CH3:28])=[N:8]3)[CH2:15]2)[CH:21]=[C:22]([Cl:27])[CH:23]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67217947HCID 67217947, compound

Product 1

HCID 67217792HCID 67217792, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of ethyl ester of example 17.3 (493 mg) in 10 ml THF:water (4:1) was added sodium hydroxide (68 mg). The reaction mixture was stirred at room temperature for 3 hours before adding 2 ml of methanol. The reaction was stirred overnight before evaporation of the solvent in vacuo. The aqueous layer was extracted with ethyl acetate before being acidified. It was then extracted several times with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to afford a mixture of regioisomeric acids (224 mg, 3-methyl major and 5-methyl minor). 1H-NMR (CDCl3, 400 MHz): 8.5 (s, 1H), 7.5 (m, 2H), 7.45 (m, 1H), 4.35 (d, 1H), 3.85 (d, 1H), 2.50 (s, 3H).

Workup

  1. stirringThe reaction was stirred overnight before evaporation of the solvent in vacuo
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. extractionIt was then extracted several times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. customto afford
  7. additiona mixture of regioisomeric acids (224 mg, 3-methyl major and 5-methyl minor)

Sources & evidence

ORD record
ord-29f903d4254d43f8bdef2991fdc824c3
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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