Morpholine → (3EZ,5R)-1-(biphenyl-4-ylcarbonyl)-5-(3-morpholin-4-yl-3-oxopropyl) pyrrolidin-3-one O-methyloxime

HRID 225969Notes

Reaction equation

HRID 225969 reaction equation
[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:13][C:12](=[N:14][O:15][CH3:16])[CH2:11][C@H:10]2[CH2:17][CH2:18][C:19]([OH:21])=O)=[O:8])=[CH:3][CH:2]=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>>[CH3:16][O:15][N:14]=[C:12]1[CH2:11][C@@H:10]([CH2:17][CH2:18][C:19]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:21])[N:9]([C:7]([C:4]2[CH:5]=[CH:6][C:1]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:2][CH:3]=2)=[O:8])[CH2:13]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 1317275283-[(2R,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]propanoic acid2×

Product 1

HCID 131727531(3EZ,5R)-1-(biphenyl-4-ylcarbonyl)-5-(3-morpholin-4-yl-3-oxopropyl) pyrrolidin-3-one O-methyloximeYield 97%

Procedure

The same method as employed in the preparation of Example 7, but starting from 3-[(2R,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]propanoic acid (Intermediate 8) and morpholine, gave the title compound. Yield: 97%. HPLC purity: 96%

Workup

  1. customThe same method as employed in the preparation of Example 7

Sources & evidence

ORD record
ord-a82922b5dc5b415db84e450fa3a5436c
Source dataset
uspto-grants-2009_07
Patent number
US07557136B2

Reaction notes

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