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

HRID 1629712Notes

Reaction equation

HRID 1629712 reaction equation
C[O:2][C:3]([C:5]1([CH3:28])[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C@@H:17]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([CH3:27])[CH:21]=3)[CH2:18][CH3:19])[CH:11]=2)[CH2:6]1)=[O:4].[Li+].[OH-].Cl>C1COCC1>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C@H:17]([NH:16][C:12]2[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=2)[CH2:9][N:7]2[CH2:6][C:5]([CH3:28])([C:3]([OH:4])=[O:2])[CH2:8]2)[CH2:18][CH3:19])=[CH:21][C:22]=1[CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 673297101-{3-[(R)-1-(4-Chloro-3-methyl-phenyl)-propylamino]-benzyl}-3-methyl-azetidine-3-carboxylic acid methyl ester

Product 1

HCID 533404321-{3-[(R)-1-(4-Chloro-3-methyl-phenyl)-propylamino]-benzyl}-3-methyl-azetidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of INT 15 (158 mg, 0.39 mmol) in THF (3.9 mL) at 0° C. was added LiOH (1.0 M in H2O, 1.97 mL, 1.97 mmol). The reaction mixture was stirred at room temperature for 5 hours. The mixture was acidified with 1 M HCl and concentrated. The residue was taken up in CH2Cl2/EtOAc and washed with brine. The aqueous layer was extracted with CH2Cl2/EtOAc (3×). The combined organic layers were dried over MgSO4 and concentrated. The residue was purified by preparative HPLC (H2O/CH3CN) to afford the title compound Example 8.

Workup

  1. concentrationconcentrated
  2. washwashed with brine
  3. extractionThe aqueous layer was extracted with CH2Cl2/EtOAc (3×)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC (H2O/CH3CN)

Sources & evidence

ORD record
ord-76fd93cb952e4f1c8ae53f44d2620e33
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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