Hydrochloric Acid → 1-{3-[1-(4-Chloro-3-methyl-phenyl)-ethylamino]-benzyl}-azetidine-3-carboxylic acid

HRID 1629699Notes

Reaction equation

HRID 1629699 reaction equation
C[O:2][C:3]([CH:5]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][CH:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH3:26])[CH:20]=3)[CH3:18])[CH:11]=2)[CH2:6]1)=[O:4].[Li+].[OH-].Cl>C1COCC1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([CH:17]([NH:16][C:12]2[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=2)[CH2:9][N:7]2[CH2:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:8]2)[CH3:18])=[CH:20][C:21]=1[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 673302801-{3-[1-(4-Chloro-3-methyl-phenyl)-ethylamino]-benzyl}-azetidine-3-carboxylic acid methyl ester

Product 1

HCID 533403171-{3-[1-(4-Chloro-3-methyl-phenyl)-ethylamino]-benzyl}-azetidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of INT 4 (85 mg, 0.23 mmol) in THF (2.2 mL) was added 1 M LiOH (1.1 mL, 1.14 mmol). The resulting mixture was stirred at room temperature for 19 hours. The mixture was acidified to pH 5 with 1 M HCl. The organic solvent was removed. More 1 M HCl was added to adjust the pH to 3. The mixture was extracted with EtOAc (3×). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (CH2Cl2/MeOH) to give Example 1.

Workup

  1. customThe organic solvent was removed
  2. additionMore 1 M HCl was added
  3. extractionThe mixture was extracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (CH2Cl2/MeOH)
  8. customto give Example 1

Sources & evidence

ORD record
ord-c7882aacc9584805bf963b2c8aa982c6
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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