Water → HCID 69516070, compound

HRID 458461Notes

Reaction equation

HRID 458461 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[NH:14][C:15]([CH2:38][CH2:39][C:40]([F:43])([F:42])[F:41])=[C:16]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:17]([C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=2)[C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[N+]([O-])([O-])=O.[NH4+].[Ce]>C(#N)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:17]([C:24]2[CH:25]=[CH:26][C:27]([C:28]([OH:30])=[O:29])=[CH:31][CH:32]=2)[C:16]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:15]([CH2:38][CH2:39][C:40]([F:43])([F:42])[F:41])[N:14]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 57418452Ammonium cerium-nitrateHCID 69516063HCID 69516063, compound

Product 1

HCID 69516070HCID 69516070, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[2-[(2S)-1-(tert-butoxycarbonyl)pyrrolidinyl]-3,5-bis(ethoxycarbonyl)-6-(3,3,3-trifluoropropyl)-1,4-dihydro-4-pyridinyl]benzoic acid (3.21 g, 6.91 mmol) was dissolved in a 50:50 mixture of acetonitrile:H2O. To the mixture cerium ammonium nitrate was added (8.96 g, 13.8 mmol) and stirred for 45 minutes. The reaction mixture was dissolved in 100 mL of ethyl acetate and washed with H2O (2×50 mL) and brine. The organics were then dried over sodium sulfate, filtered and concentrated to yield a orange/red oil that was purified by column chromatography (ethyl acetate/hexanes (4:1)). Mixture carried on without purification.

Workup

  1. washwashed with H2O (2×50 mL) and brine
  2. dry with materialThe organics were then dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield a orange/red oil that
  6. customwas purified by column chromatography (ethyl acetate/hexanes (4:1))
  7. customMixture carried on without purification

Sources & evidence

ORD record
ord-7b0705e087b740b0a8558eee7b798479
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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