Ceric ammonium nitrate → HCID 69939660, compound

HRID 1058252Notes

Reaction equation

HRID 1058252 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:71]1[CH2:76][CH2:75][CH2:74][CH2:73][CH2:72]1)([C:38]([N:40]1[CH2:70][CH2:69][CH2:68][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:59]C1C=CC(OC)=CC=1)[C:55]([F:58])([F:57])[F:56])=[O:43])=[O:39])N)=[O:34])([CH3:31])([CH3:30])[CH3:29]>O.CC#N>[NH2:59][CH:54]([C:55]([F:58])([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[CH2:68][CH2:69][CH2:70][N:40]1[C:38](=[O:39])[C@H:36]([NH:35][C:33]([O:32][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:34])[CH:71]1[CH2:72][CH2:73][CH2:74][CH2:75][CH2:76]1

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 69938964HCID 69938964, compound

Product 1

HCID 69939660HCID 69939660, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of CAN (1.259 g, 2.30 mmol) in water (12 mL) was added to a stirred solution of 1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylglycyl}-N-(5-chloro-2-{3,3,3-trifluoro-2-[(4-methoxyphenyl)amino]propyl}benzyl)-L-prolinamide (0.798 g, 1.15 mmol) in CH3CN (20 mL) at 0° C. and the resulting solution was warmed to ambient temperature. The solution was partitioned between EtOAc and 10% aqueous NH4OH and 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 column chromatography on silica (eluting with 1-10% of 10% ammonium hydroxide in methanol/chloroform gradient) to give N-[2-(2-amino-3,3,3-trifluoropropyl)-5-chlorobenzyl]-1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-L-prolinamide (0.282 g) as a foam; MS m/z=589.6.

Workup

  1. customThe solution was partitioned between EtOAc and 10% aqueous NH4OH
  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 column chromatography on silica (eluting with 1-10% of 10% ammonium hydroxide in methanol/chloroform gradient)

Sources & evidence

ORD record
ord-ec94314c359442cf9d04337abafbd81a
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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