(2-Chloro-4-fluorophenyl)acetyl chloride → rac-1-{3-[2-(2-Chloro-4-fluoro-phenyl)-acetylamino]-benzyl}-pyrrolidine-3-carboxylic acid

HRID 1486724Notes

Reaction equation

HRID 1486724 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10](Cl)=[O:11].ClC1C=CC(C(NC2C=CC=C(C3OCCO3)C=2)=O)=CC=1.N1CCC(C(OC)=O)C1.C([O:45][C:46]([CH:48]1[CH2:53][CH2:52][N:51]([CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[C:57]([NH:61]C(=O)C3C=CC(Cl)=CC=3)[CH:56]=2)[CH2:50]C1)=[O:47])C>>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([NH:61][C:57]1[CH:56]=[C:55]([CH:60]=[CH:59][CH:58]=1)[CH2:54][N:51]1[CH2:52][CH2:53][CH:48]([C:46]([OH:45])=[O:47])[CH2:50]1)=[O:11]

Participants

5

Reactant 4

HCID 2757568(2-Chloro-4-fluorophenyl)acetyl chlorideHCID 4114360Methyl Pyrrolidine-3-carboxylateHCID 867065474-Chloro-N-(3-[1,3]dioxolan-2-yl-phenyl)-benzamideHCID 867065481-[3-(4-Chloro-benzoylamino)-benzyl]-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 131736811rac-1-{3-[2-(2-Chloro-4-fluoro-phenyl)-acetylamino]-benzyl}-pyrrolidine-3-carboxylic acid

Procedure

The title compound is prepared according to the reaction sequence 2.001a-2.001d described above using 2-(2-chloro-4-fluorophenyl)acetyl chloride instead of 4-chlorobenzoyl chloride as in 2.001a and methyl pyrrolidine-3-carboxylate instead of ethyl isonipecotate as in 2.001c: LC-MS A: tR=0.63 min; [M+H]+=391.01.

Sources & evidence

ORD record
ord-bfacaabcfc2345b89cbcb35fca2c9e04
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

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