2-bromo-N-(isoxazol-3-yl)acetamide → (R)-3-[2-Hydroxy-2-(4-methoxy-phenyl)-2-phenyl-acetoxy]-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 660095Notes

Reaction equation

HRID 660095 reaction equation
[Br:1][CH2:2][C:3]([NH:5][C:6]1[CH:10]=[CH:9][O:8][N:7]=1)=[O:4].[N:11]12[CH2:18][CH2:17][CH:14]([CH2:15][CH2:16]1)[C@@H:13]([O:19][C:20](=[O:37])[C:21]([OH:36])([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:12]2>C(Cl)(Cl)Cl>[Br-:1].[OH:36][C:21]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:20]([O:19][C@@H:13]1[CH:14]2[CH2:15][CH2:16][N+:11]([CH2:2][C:3](=[O:4])[NH:5][C:6]3[CH:10]=[CH:9][O:8][N:7]=3)([CH2:18][CH2:17]2)[CH2:12]1)=[O:37]

Participants

4

Reactant 2

HCID 133629192-bromo-N-(isoxazol-3-yl)acetamideHCID 86627868Hydroxy-(4-methoxy-phenyl)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester2×

Product 1

HCID 11671405(R)-3-[2-Hydroxy-2-(4-methoxy-phenyl)-2-phenyl-acetoxy]-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
50 °C

Procedure

To a stirred solution of bromo-N-isoxazol-3-yl-acetamide (Intermediate Ai) (0.057 g, 0.278 mmol) in dry chloroform (1 ml) heated to 50° C. is added hydroxy-(4-methoxy-phenyl)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Intermediate O) in chloroform (1 ml). The reaction mixture is stirred at 50° C. for 6 hours after which time, the titled product is detected by LC-MS. (M+ 492.3)

Sources & evidence

ORD record
ord-f973b73ed66d4e39a63b4d639b637e15
Source dataset
uspto-grants-2011_12
Patent number
US08084463B2

Reaction notes

Loading…