3-(1-TERT-BUTOXYCARBONYLPIPERAZIN-4-YL)PROPIONIC ACID → tert-butyl 4-(2-{3-[(2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-4-(methoxyimino)pyrrolidinyl]-1,2,4-oxadiazol-5-yl}ethyl)-1-piperazinecarboxylate

HRID 1242589Notes

Reaction equation

HRID 1242589 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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[C:17](=[N:19][OH:20])[NH2:18])=[O:8])=[CH:3][CH:2]=1.[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][C:42](O)=O)[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>>[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:2]=[CH:3][C:4]([C:7]([N:9]2[CH2:13][C:12](=[N:14][O:15][CH3:16])[CH2:11][C@H:10]2[C:17]2[N:18]=[C:42]([CH2:41][CH2:40][N:37]3[CH2:38][CH2:39][N:34]([C:32]([O:31][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:33])[CH2:35][CH2:36]3)[O:20][N:19]=2)=[O:8])=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 27356443-(1-TERT-BUTOXYCARBONYLPIPERAZIN-4-YL)PROPIONIC ACIDHCID 90995821(2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-N'-hydroxy-4-(methoxyimino)-2-pyrrolidinecarboximidamide2×

Product 1

HCID 58714591tert-butyl 4-(2-{3-[(2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-4-(methoxyimino)pyrrolidinyl]-1,2,4-oxadiazol-5-yl}ethyl)-1-piperazinecarboxylateYield 70%

Procedure

Following the general method as outlined in Example 15, starting from (2S,4EZ)-1-([1,1′-biphenyl]-4-ylcarbonyl)-N′-hydroxy-4-(methoxyimino)-2-pyrrolidinecarboximidamide (Intermediate 8) and 3-[4-(tert-butoxycarbonyl)-1-piperazinyl]propanoic acid, the title compound was obtained in 70% yield (78% purity by HPLC).

Sources & evidence

ORD record
ord-8738e6f7e6a44b4bbc7e34418d63b33d
Source dataset
uspto-grants-2006_10
Patent number
US07115639B2

Reaction notes

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