Ceric ammonium nitrate → HCID 69939192, compound

HRID 1058248Notes

Reaction equation

HRID 1058248 reaction equation
O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].[C:28]([O:32][C:33]([NH:35][C@:36]([CH:70]1[CH2:75][CH2:74][CH2:73][CH2:72][CH2:71]1)([C:38]([N:40]1[CH2:69][CH2:68][CH2:67][C@H:41]1[C:42]([NH:44][CH2:45][C:46]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:47]=1[CH2:53][CH:54]([NH:58]C1C=CC(OC)=CC=1)[CH:55]([F:57])[F:56])=[O:43])=[O:39])N)=[O:34])([CH3:31])([CH3:30])[CH3:29]>O.CC#N>[NH2:58][CH:54]([CH:55]([F:57])[F:56])[CH2:53][C:47]1[CH:48]=[CH:49][C:50]([Cl:52])=[CH:51][C:46]=1[CH2:45][NH:44][C:42](=[O:43])[C@@H:41]1[CH2:67][CH2:68][CH2:69][N:40]1[C:38](=[O:39])[C@H:36]([NH:35][C:33]([O:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:34])[CH:70]1[CH2:71][CH2:72][CH2:73][CH2:74][CH2:75]1

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 69938103HCID 69938103, compound

Product 1

HCID 69939192HCID 69939192, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of CAN (0.274 g, 0.50 mmol) in water (2.0 mL) was added to a stirred solution of 1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylglycyl}-N-(5-chloro-2-{3,3-difluoro-2-[(4-methoxyphenyl)amino]propyl}benzyl)-L-prolinamide (0.168 g, 0.25 mmol) in CH3CN (3.0 mL) at 0° C. and the resulting solution was warmed to ambient temperature. After 18 h the solution was partitioned between EtOAc(20 mL) and 10% aqueous NH4OH (10 mL). The resulting two phase suspension was filtered and the organic layer was washed with 10% sodium sulfite and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (eluting with 5% methylene chloride, 70% ethyl acetate/hexanes followed by ammonium hydroxide/methanol/chloroform, 1:9:90) to give N-[2-(2-amino-3,3-difluoropropyl)-5-chlorobenzyl]-1-{(2R)-2-[(tert-butoxycarbonyl)amino]2-cyclohexylethanoyl}-L-prolinamide (0.0801 g) as an oil; MS m/z=571.4.

Workup

  1. customAfter 18 h the solution was partitioned between EtOAc(20 mL) and 10% aqueous NH4OH (10 mL)
  2. filtrationThe resulting two phase suspension was filtered
  3. washthe organic layer was washed with 10% sodium sulfite and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by flash chromatography (eluting with 5% methylene chloride, 70% ethyl acetate/hexanes followed by ammonium hydroxide/methanol/chloroform, 1:9:90)

Sources & evidence

ORD record
ord-c6dd50b89c3b48e58763325611d36c87
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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