Water → HCID 69515707, compound

HRID 458457Notes

Reaction equation

HRID 458457 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][CH2:40][CH:41]([CH3:43])[CH3:42])=[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][CH2:40][CH:41]([CH3:43])[CH3:42])[N:14]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 57418452Ammonium cerium-nitrateHCID 69516365HCID 69516365, compound

Product 1

HCID 69515707HCID 69515707, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[2-[(2S)-1-(tert-butoxycarbonyl)pyrrolidinyl]-3,5-bis(ethoxycarbonyl)-6-(4-methylpentyl)-1,4-dihydro-4-pyridinyl]benzoic acid was dissolved in a 50:50 mixture of acetonitrile:H2O. To the mixture cerium ammonium nitrate was added (6.65 g, 10.3 mmol) and allowed to stir 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 which was purified by column chromatography (ethyl acetate/hexanes (4:1)) to give 2.0 g of a solid.

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 which
  6. customwas purified by column chromatography (ethyl acetate/hexanes (4:1))

Sources & evidence

ORD record
ord-5e829474c65a4027a50b2685d75b3a86
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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