Trifluoroacetic acid methylene chloride → cis(+/-)-{(5Z)-5-[2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-oxoethylidene]-2,4-dioxo-1,3-thiazolidin-3-yl}acetic acid

HRID 1425231Notes

Reaction equation

HRID 1425231 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:35])/[CH:19]=[C:20]3/[C:21](=[O:34])[N:22]([CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])[C:23](=[O:25])[S:24]/3)[CH2:14][C@H:13]2[O:36][CH3:37])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].FC(F)(F)C(O)=O.ClCCl>CO>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:35])/[CH:19]=[C:20]3/[C:21](=[O:34])[N:22]([CH2:26][C:27]([OH:29])=[O:28])[C:23](=[O:25])[S:24]/3)[CH2:14][C@H:13]2[O:36][CH3:37])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86648706tert-Butyl cis(+/-)-{(5Z)-5-[2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-oxoethylidene]-2,4-dioxo-1,3-thiazolidin-3-yl}acetate

Product 1

HCID 86648705cis(+/-)-{(5Z)-5-[2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-oxoethylidene]-2,4-dioxo-1,3-thiazolidin-3-yl}acetic acidYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl cis(±)-{(5Z)-5-[2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-oxoethylidene]-2,4-dioxo-1,3-thiazolidin-3-yl}acetate obtained in Example (163a) (20.4 mg, 0.04 mmol) was dissolved in methanol (4 mL). A 20% trifluoroacetic acid-dichloromethane solution (5 ml) was added, and the mixture was stirred at room temperature. The organic solvent was evaporated under reduced pressure, and then the residue was washed with ether. The solid was collected by filtration to obtain 7.79 mg of the title compound as a white solid (43%).

Workup

  1. customThe organic solvent was evaporated under reduced pressure
  2. washthe residue was washed with ether
  3. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-0c59ad9d6c9f46449f1d2ca990b9eee5
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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