3-(S)-aminomethyl-1-(2,3-dichlorobenzyl)pyrrolidine → N-[1-(2,3-dichlorobenzyl)pyrrolidin-3-(S)-ylmethyl]-2-(3-acetylaminophenyl)-acetamide

HRID 1276375Notes

Reaction equation

HRID 1276375 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=O)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].NCC1CCN(CC2C=CC(Cl)=C(Cl)C=2)C1.[NH2:31][CH2:32][C@@H:33]1[CH2:37][CH2:36][N:35]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[C:40]=2[Cl:46])[CH2:34]1>>[Cl:46][C:40]1[C:41]([Cl:45])=[CH:42][CH:43]=[CH:44][C:39]=1[CH2:38][N:35]1[CH2:36][CH2:37][C@@H:33]([CH2:32][NH:31][C:12](=[O:14])[CH2:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=2)[CH2:34]1

Participants

4

Reactant 3

HCID 206387783-(S)-aminomethyl-1-(2,3-dichlorobenzyl)pyrrolidineHCID 218918092-(3-Acetamidophenyl)acetic acidHCID 221153103-Aminomethyl-1-(3,4-dichlorobenzyl)pyrrolidine

Product 1

HCID 20638776N-[1-(2,3-dichlorobenzyl)pyrrolidin-3-(S)-ylmethyl]-2-(3-acetylaminophenyl)-acetamide

Procedure

Proceeding as described above but substituting 4-(2,5-dimethylphenyl)-4-oxobutyric acid with 2-(3-acetylaminophenyl)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-acetylaminophenyl)-acetamide.

Sources & evidence

ORD record
ord-dd1b517a8fbe4987b7222690d60b50f4
Source dataset
uspto-grants-2000_12
Patent number
US06166015

Reaction notes

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