4-(Hydroxymethyl)benzoic acid → (3Ez,5s)-1-([1,1'-biphenyl]-4-ylcarbonyl)-5-{5-[4-(hydroxymethyl)phenyl]-1,2,4-oxadiazol-3-yl}-3-pyrrolidinone o-methyloxime

HRID 1242566Notes

Reaction equation

HRID 1242566 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.[OH:27][CH2:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=O)=[CH:31][CH:30]=1>>[CH3:16][O:15][N:14]=[C:12]1[CH2:11][C@@H:10]([C:17]2[N:18]=[C:33]([C:32]3[CH:36]=[CH:37][C:29]([CH2:28][OH:27])=[CH:30][CH:31]=3)[O:20][N:19]=2)[N:9]([C:7]([C:4]2[CH:3]=[CH:2][C:1]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:6][CH:5]=2)=[O:8])[CH2:13]1

Participants

3

Reactant 2

HCID 763604-(Hydroxymethyl)benzoic acidHCID 90995821(2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-N'-hydroxy-4-(methoxyimino)-2-pyrrolidinecarboximidamide2×

Product 1

HCID 58714546(3Ez,5s)-1-([1,1'-biphenyl]-4-ylcarbonyl)-5-{5-[4-(hydroxymethyl)phenyl]-1,2,4-oxadiazol-3-yl}-3-pyrrolidinone o-methyloxime

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 4-(hydroxymethyl)benzoic acid, the title compound was obtained in 54% purity by HPLC. MS(ESI+): m/z=469.4.

Sources & evidence

ORD record
ord-85b0f57985094d85823c83374a576603
Source dataset
uspto-grants-2006_10
Patent number
US07115639B2

Reaction notes

Loading…