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

HRID 1629703Notes

Reaction equation

HRID 1629703 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[CH:15]=O)[CH2:9][CH3:10])=[CH:4][C:3]=1[CH3:20].[NH:21]1[CH2:24][CH:23]([C:25]([OH:27])=[O:26])[CH2:22]1.CC(O)=O>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[CH2:15][N:21]2[CH2:24][CH:23]([C:25]([OH:27])=[O:26])[CH2:22]2)[CH2:9][CH3:10])=[CH:4][C:3]=1[CH3:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 931923-azetidinecarboxylic AcidHCID 575173193-[(R)-1-(4-Chloro-3-methyl-phenyl)-propylamino]-benzaldehyde

Product 1

HCID 533403191-{3-[(R)-1-(4-Chloro-3-methyl-phenyl)-propylamino]-benzyl}-azetidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of INT 7 (700 mg, 2.43 mmol) and azetidine-3-carboxylic acid (248 mg, 2.92 mmol) in MeOH (24 mL) was added HOAc (0.14 mL, 2.43 mmol) followed by PS—CNBH3 (2.5 mmol/g, 1.95 g, 4.86 mmol). The reaction mixture was stirred at room temperature for 3 days. The mixture was filtered over Celite. The filtrate was concentrated. The residue was purified by preparative HPLC (H2O/CH3CN) to give the title compound Example 3.

Workup

  1. filtrationThe mixture was filtered over Celite
  2. concentrationThe filtrate was concentrated
  3. customThe residue was purified by preparative HPLC (H2O/CH3CN)

Sources & evidence

ORD record
ord-80542b3716d1495eb2d31410b615111f
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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