Cesium carbonate → 4-((S)-4-Carboxy-2-{[5-(1-carboxy-ethoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid ethyl ester

HRID 1908644Notes

Reaction equation

HRID 1908644 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:38])[C@@H:13]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([OH:31])[N:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2].Br[CH:40]([CH3:46])[C:41]([O:43]CC)=[O:42].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:38])[C@@H:13]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([O:31][CH:40]([C:41]([OH:43])=[O:42])[CH3:46])[N:28]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 79040Ethyl 2-bromopropionateHCID 178473388HCID 178473388, compound

Product 1

HCID 668547744-((S)-4-Carboxy-2-{[5-(1-carboxy-ethoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.50 g 4-{(S)-4-tert-butoxycarbonyl-2-[(5-hydroxy-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester in 12 ml DMF were added 670 μl ethyl 2-bromopropionate and 3.2 g cesium carbonate. After stirring at RT for 24 h the solution was diluted with ethyl acetate and extracted with aqueous LiCl (4% w/w). The crude product obtained after evaporation of the solvent was dissolved in THF and treated with 1 N NaOH. When conversion was complete (4 h) Amberlite IR-120® was added, the suspension filtrated and the filtrate evaporated to give the crude product (1.56 g)

Workup

  1. extractionextracted with aqueous LiCl (4% w/w)
  2. customThe crude product obtained
  3. customafter evaporation of the solvent
  4. dissolutionwas dissolved in THF
  5. additiontreated with 1 N NaOH
  6. custom(4 h) Amberlite IR-120®
  7. additionwas added
  8. filtrationthe suspension filtrated
  9. customthe filtrate evaporated

Sources & evidence

ORD record
ord-a923d9f09cae463685ad30a85032b298
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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