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

HRID 1629728Notes

Reaction equation

HRID 1629728 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[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[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[F:10])[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 1736043-Bromo-4-fluorobenzaldehydeHCID 57517333(R)-1-(4-chloro-3-methyl-phenyl)-propylamine hydrochloride

Product 1

HCID 533407961-{3-[(R)-1-(4-Chloro-3-methyl-phenyl)-propylamino]-4-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-4-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-84dd25580f7d41f68b40105c85b2475b
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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