Sodium Carbonate → HCID 58714545, compound

HRID 1242599Notes

Reaction equation

HRID 1242599 reaction equation
C([O:5][CH2:6][C@@H:7]([C:16]1[O:20][N:19]=[C:18]([C@@H:21]2[CH2:25][C:24](=[N:26][O:27][CH3:28])[CH2:23][N:22]2[C:29]([C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:33][CH:32]=2)=[O:30])[N:17]=1)[NH:8]C(OC(C)(C)C)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:28][O:27][N:26]=[C:24]1[CH2:25][CH2:21][N:22]([C:29]([C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:33][CH:32]=2)=[O:30])[CH2:23]1.[CH3:28][O:27][N:26]=[C:24]1[CH2:25][C@@H:21]([C:18]2[N:17]=[C:16]([C@@H:7]([NH2:8])[CH2:6][OH:5])[O:20][N:19]=2)[N:22]([C:29]([C:31]2[CH:32]=[CH:33][C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:35][CH:36]=2)=[O:30])[CH2:23]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 21863450Trifluoroacetic acid methylene chlorideHCID 58714593HCID 58714593, compound

Product 2

HCID 58714545HCID 58714545, compoundHCID 88093719HCID 88093719, compound

Procedure

4-{[(2S,4EZ)-2-(5-{(1S)-2-tert-butoxy-1-[(tert-butoxycarbonyl)amino]ethyl}-1,2,4-oxadiazol-3-yl)-4-(methoxyimino)pyrrolidinyl]carbonyl}-1,1′-biphenyl (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 two products, which were separated and purified by flash-chromatography to give the desired products as mixtures of E-/Z-isomers, (3EZ,5S)-5-{5-[(1S)-1-amino-2-tert-butoxyethyl]-1,2,4-oxadiazol-3-yl}-1-([1,1′-biphenyl]-4-ylcarbonyl-3-pyrrolidinone O-methyloxime in 20% yield (80.8% purity by HPLC), and (3EZ,5S)-5-{5-[(1S)-1-amino-2-hydroxyethyl]-1,2,4-oxadiazol-3-yl}-1-([1,1′-biphenyl]-4-ylcarbonyl)-3-pyrrolidinone O-methyloxime in 30% yield (98.1% purity by HPLC).

Workup

  1. extractionextracted with DCM
  2. dry with materialdried over magnesium sulfate and solvent removal
  3. customafforded two products, which
  4. customwere separated
  5. custompurified by flash-chromatography

Sources & evidence

ORD record
ord-ea91b28dafd945ed88384eef0194983e
Source dataset
uspto-grants-2006_10
Patent number
US07115639B2

Reaction notes

Loading…