Cesium carbonate → HCID 68601852, compound

HRID 1185423Notes

Reaction equation

HRID 1185423 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:34])[C@@H:13]([NH:19][C:20]([C:22]2[CH:31]=[C:30]([OH:32])[C:29]3[C:24](=[CH:25][C:26]([CH3:33])=[CH:27][CH:28]=3)[N:23]=2)=[O:21])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:42][C:43]([N:45]1[CH2:49][CH2:48][CH2:47][C:46]1=[O:50])=[O:44]>CN(C=O)C.O>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12](=[O:34])[C@@H:13]([NH:19][C:20]([C:22]2[CH:31]=[C:30]([O:32][CH2:42][C:43](=[O:44])[N:45]3[CH2:49][CH2:48][CH2:47][C:46]3=[O:50])[C:29]3[C:24](=[CH:25][C:26]([CH3:33])=[CH:27][CH:28]=3)[N:23]=2)=[O:21])[CH2:14][CH2:15][C:16]([O:18][C:26]([CH3:33])([CH3:27])[CH3:25])=[O:17])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 31612511-(2-Chloro-acetyl)-pyrrolidin-2-oneHCID 178473392HCID 178473392, compound

Product 1

HCID 68601852HCID 68601852, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 200 mg of 4-{(S)-4-Carboxy-2-[(4-hydroxy-7-methyl-quinoline-2-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester in 2.5 ml of DMF, 184 mg of cesium carbonate and 91 mg of 1-(2-Chloro-acetyl)-pyrrolidin-2-one was added and the reaction mixture was stirred for 3 days at RT. Then, the reaction mixture was diluted with water and filtered through a chem Elut® cartridge by eluting with ethyl acetate. The solvents were removed under reduced pressure and the isolated crude product was pure enough for the next reaction step.

Workup

  1. filtrationfiltered through a chem Elut® cartridge
  2. washby eluting with ethyl acetate
  3. customThe solvents were removed under reduced pressure
  4. customthe isolated crude product
  5. customwas pure enough for the next reaction step

Sources & evidence

ORD record
ord-cc07be2e5bc34d10b1f5079ef477c517
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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