3-azetidinecarboxylic Acid → 1-{3-[(R)-1-(4-Chloro-3-methyl-phenyl)-propylamino]-2-fluoro-benzyl}-azetidine-3-carboxylic acid

HRID 1629727Notes

Reaction equation

HRID 1629727 reaction equation
Br[C:2]1[C:3]([F:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.Cl.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C@H:19]([NH2:22])[CH2:20][CH3:21])=[CH:15][C:14]=1[CH3:23].[NH:24]1[CH2:27][CH:26]([C:28]([OH:30])=[O:29])[CH2:25]1>>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C@H:19]([NH:22][C:2]2[C:3]([F:10])=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH2:5][N:24]2[CH2:27][CH:26]([C:28]([OH:30])=[O:29])[CH2:25]2)[CH2:20][CH3:21])=[CH:15][C:14]=1[CH3:23]

Participants

4

Reactant 3

HCID 931923-azetidinecarboxylic AcidHCID 220193613-Bromo-2-fluorobenzaldehydeHCID 57517333(R)-1-(4-chloro-3-methyl-phenyl)-propylamine hydrochloride

Product 1

HCID 533406761-{3-[(R)-1-(4-Chloro-3-methyl-phenyl)-propylamino]-2-fluoro-benzyl}-azetidine-3-carboxylic acid

Procedure

The title compound was prepared according to Scheme 3 following a procedure analogous to steps 3 to 6 of Example 21 using 3-bromo-2-fluoro-benzaldehyde in step 3, (R)-1-(4-chloro-3-methyl-phenyl)-propylamine hydrochloride in step 4 and azetidine-3-carboxylic acid in step 6.

Sources & evidence

ORD record
ord-d0df338a33a248a19e8f024318d0b005
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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