Lithium Hydroxide → HCID 10389076, compound

HRID 2121182Notes

Reaction equation

HRID 2121182 reaction equation
C[O:2][C:3](=[O:33])[C@H:4]([CH2:29][CH2:30][S:31][CH3:32])[NH:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:9][C:8]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27].[Li+].[OH-]>C1COCC1>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([NH:5][C@H:4]([C:3]([OH:33])=[O:2])[CH2:29][CH2:30][S:31][CH3:32])=[O:28])=[C:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])[CH:9]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 20622802HCID 20622802, compound

Product 1

HCID 10389076HCID 10389076, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The [4-(3-pyridyloxymethyl)-2-(2-methylphenyl)benzoyl]methionine methyl ester prepared in Example 204F (72 mg, 0.15 mmol) was dissolved in 3 mL of THF and 1 mL of saturated aqueous LiOH was added. The reaction mixture was stirred at room temperature for 1 hour. The reaction was thoroughly evaporated and formic acid was added until pH=3 was obtained at which time the reaction was evaporated to dryness and 10 mL of ethyl acetate was added followed by a minimum quantity of H2O (1 mL) to completely solubilize the free acid and the water soluble salts, respectively. The layers were separated and the aqueous layer was extracted with ethyl acetate (3×5 mL). The ethyl acetate layers were combined, dried over Na2SO4, filtered and evaporated to give 58 mg (84%) of [4-(3-pyridyloxymethyl)-2-(2-methylphenyl)benzoyl]methionine as an amorphous solid. 1H NMR (300 mHz, CD3OD) δ 8.30 (d, 1H), 8.15 (dd, 1H), 7.68 (bd, 1H), 7.58-7.48 (m, 2H), 7.40-7.30 (m, 2H), 7.26-7.16 (m, 4H), 5.25 (s, 2H), 4.50-4.40 (m, 1H), 2.20-2.02 (m, 5H), 2.00 (s, 3H), 2.00-1.90 (m, 1H), 1.80-1.68 (m, 1H) CIMS MH+ 451.

Workup

  1. customThe reaction was thoroughly evaporated
  2. additionformic acid was added until pH=3
  3. customwas obtained at which time the reaction
  4. customwas evaporated to dryness and 10 mL of ethyl acetate
  5. additionwas added
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with ethyl acetate (3×5 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-5976cd173c32448883689a4e85d7f286
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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