Sodium Carbonate → HCID 66915942, compound

HRID 1783472Notes

Reaction equation

HRID 1783472 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:13][N:12]=[N:11][N:10]=1.[C:14]([O:18][C:19]([N:21]1[CH2:25][C@H:24](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:23][C@H:22]1[C:37](N1CCN(C2C=CC=CC=2C#N)CC1)=[O:38])=[O:20])([CH3:17])([CH3:16])[CH3:15].[C:53](=O)([O-])[O-:54].[Na+].[Na+]>CN(C=O)C.CC(=O)OCC>[CH3:53][O:54][C:37]([C@@H:22]1[CH2:23][C@H:24]([N:11]2[N:12]=[N:13][C:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])=[N:10]2)[CH2:25][N:21]1[C:19]([O:18][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:20])=[O:38]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 86625268HCID 86625268, compoundHCID 178505597HCID 178505597, compound

Product 1

HCID 66915942HCID 66915942, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2,4-difluoro-phenyl)-tetrazole (0.44 g, 1.1 mmol) in 5 ml DMF was added 0.1 g (0.55 mmol) of (2S,4R)-2-[4-(2-cyano-phenyl)-piperazine-1-carbonyl]-4-(toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester and anhydrous sodium carbonate (0.15 g, 1.4 mmol). The mixture was stirred vigorously at 60 degree overnight. The solution was diluted with 30 ml EA and washed with 1M Na2CO3, 5% citric acid and brine, dried and concentrated to give the crude product as yellow oil (0.14 g, 0.34 mmol). MS m/e=410.3 [M+H]+.

Workup

  1. washwashed with 1M Na2CO3, 5% citric acid and brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-96039615c0384ebc918f9beb2e65bb35
Source dataset
uspto-grants-2009_03
Patent number
US07501422B2

Reaction notes

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