3-Fluoro-4-hydroxybenzeneacetic acid → N-[1-(2,3-dichlorobenzyl)pyrrolidin-3-(S)-ylmethyl]-2-(3-fluoro-4-hydroxyphenyl)-acetamide

HRID 1276374Notes

Reaction equation

HRID 1276374 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[OH:8].NCC1CCN(CC2C=CC(Cl)=C(Cl)C=2)C1.[NH2:29][CH2:30][C@@H:31]1[CH2:35][CH2:34][N:33]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[C:38]=2[Cl:44])[CH2:32]1>>[Cl:44][C:38]1[C:39]([Cl:43])=[CH:40][CH:41]=[CH:42][C:37]=1[CH2:36][N:33]1[CH2:34][CH2:35][C@@H:31]([CH2:30][NH:29][C:10](=[O:12])[CH2:9][C:4]2[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([F:1])[CH:3]=2)[CH2:32]1

Participants

4

Reactant 3

HCID 680143-Fluoro-4-hydroxybenzeneacetic acidHCID 206387783-(S)-aminomethyl-1-(2,3-dichlorobenzyl)pyrrolidineHCID 221153103-Aminomethyl-1-(3,4-dichlorobenzyl)pyrrolidine

Product 1

HCID 20638777N-[1-(2,3-dichlorobenzyl)pyrrolidin-3-(S)-ylmethyl]-2-(3-fluoro-4-hydroxyphenyl)-acetamide

Procedure

Proceeding as described above but substituting 4-(2,5-dimethylphenyl)-4-oxobutyric acid with 2-(3-fluoro-4-hydroxyphenyl)acetic acid and 3-aminomethyl-1-(3,4-dichlorobenzyl)pyrrolidine with 3-(S)-aminomethyl-1-(2,3-dichlorobenzyl)pyrrolidine gave N-[1-(2,3-dichlorobenzyl)pyrrolidin-3-(S)-ylmethyl]-2-(3-fluoro-4-hydroxyphenyl)-acetamide.

Sources & evidence

ORD record
ord-869dab13437445e2a73e9004c99d6392
Source dataset
uspto-grants-2000_12
Patent number
US06166015

Reaction notes

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