Sodium Carbonate → HCID 58714592, compound

HRID 1242591Notes

Reaction equation

HRID 1242591 reaction equation
[C:1]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:13][C:12](=[N:14][O:15][CH3:16])[CH2:11][C@H:10]2[C:17]2[N:21]=[C:20]([CH2:22][N:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)[O:19][N:18]=2)=[O:8])=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:16][O:15][N:14]=[C:12]1[CH2:11][C@@H:10]([C:17]2[N:21]=[C:20]([CH2:22][N:23]3[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]3)[O:19][N:18]=2)[N:9]([C:7]([C:4]2[CH:5]=[CH:6][C:1]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:2][CH:3]=2)=[O:8])[CH2:13]1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 21863450Trifluoroacetic acid methylene chlorideHCID 58714564HCID 58714564, compound

Product 1

HCID 58714592HCID 58714592, compoundYield 85%

Procedure

tert-butyl 4-({3-[(2S,4EZ)-1-([1,1′-biphenyl]-4-ylcarbonyl)-4-(methoxyimino)pyrrolidinyl]-1,2,4-oxadiazol-5-yl}methyl)-1-piperazinecarboxylate (100 mg, 1.80 mmol) was treated with a 25% TFA/DCM solution at 0° C. for 1 hour. The reaction was then made basic with a sodium carbonate solution (10%) and extracted with DCM. The organic phases were combined and dried over magnesium sulfate and solvent removal afforded a residue, which was purified by flash-chromatography using dichloromethane/methanol as eluent to give the desired product, (3EZ,5S)-1-([1,1′-biphenyl]-4-ylcarbonyl)-5-[5-(1-piperazinylmethyl)-1,2,4-oxadiazol-3-yl]-3-pyrrolidinone O-methyloxime, as a mixture of E-/Z-isomers in a 85% yield (94.3% purity by HPLC).

Workup

  1. extractionextracted with DCM
  2. dry with materialdried over magnesium sulfate and solvent removal
  3. customafforded a residue, which
  4. customwas purified by flash-chromatography

Sources & evidence

ORD record
ord-ddcf331a698d41f9b64417c581d994c8
Source dataset
uspto-grants-2006_10
Patent number
US07115639B2

Reaction notes

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