Methanol → HCID 10671219, compound

HRID 2121149Notes

Reaction equation

HRID 2121149 reaction equation
C[O:2][C:3](=[O:33])[C@H:4]([CH2:29][CH2:30][S:31][CH3:32])[N:5]([C:7](=[O:28])[C:8]1[CH:13]=[CH:12][C:11](=[CH:14][NH:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH2:10][C:9]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:6].O.[OH-].[Li+].CO>C1COCC1.O>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([NH:15][CH2:14][C:11]2[CH:12]=[CH:13][C:8]([C:7]([N:5]([CH3:6])[C@H:4]([C:3]([OH:33])=[O:2])[CH2:29][CH2:30][S:31][CH3:32])=[O:28])=[C:9]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:10]=2)[CH:17]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 69930466HCID 69930466, compound

Product 1

HCID 10671219HCID 10671219, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution in THF (3.0 mL) of [4-(3-Pyridylaminomethylene)-2-phenylbenzoyl-]N-methylmethionine methyl ester (135 mg, 0.29 mmol), prepared as in Example 158, was added a solution of lithium hydroxide hydrate (20 mg, 0.49 mmol) in water (1 mL). Methanol (1 mL) and water (0.5 mL) were then added to obtain a clear solution. The reaction mixture was stirred for 1.5 hours and then the cold bath was removed and stirring was continued for 2.5 hours. The reaction mixture was partitioned between water which was taken to pH 4 with HCl and ethyl acetate. The aqueous phase was extracted three times with chloroform. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was dissolved in acetonitrile-methanol. The solution was diluted with water, frozen, and lyophilized to give [4-(3-pyridylaminomethyl)-2-phenylbenzoyl]-N-methylmethionine (120 mg) as a white powder. 1H NMR (300 MHz, D3COD) δ 7.93 (d, 1H), 7.78 (dd, 1H), 7.50 (d, 1H), 7.38 (m, 7H), 7.20 (m, 1H), 7.12 (m, 1H), 5.20 and 4.55 (both m, total 1H), 4.45 (s, 2H), 2.70 and 2.45 (both br s, total 3H), 2.24 and 2.10 (both m, total 2H), 2.00 (br s, 3H), 1.80 and 1.68 (both m, 2H); MS (DCI-NH3) m/e 450 (M+H)+. Anal calcd for C25H27N3O3S.0.65 HCl: C, 63.45; H, 5.89; N, 8.88. Found: C, 63.51; H, 5.54; N, 8.53.

Workup

  1. customto obtain a clear solution
  2. customthe cold bath was removed
  3. stirringstirring
  4. waitwas continued for 2.5 hours
  5. customThe reaction mixture was partitioned between water which
  6. extractionThe aqueous phase was extracted three times with chloroform
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. dissolutionThe residue was dissolved in acetonitrile-methanol
  11. additionThe solution was diluted with water
  12. temperaturefrozen

Sources & evidence

ORD record
ord-902f6b5809714cc7a9eef80638efe9df
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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