Pyridine → Jtp-4819

HRID 1735400Notes

Reaction equation

HRID 1735400 reaction equation
COC1C=CC([O:7][CH2:8][C:9]([C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([C@@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:23]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])=[O:17])=[O:10])=CC=1.N1C=CC=CC=1.[N+]([O-])([O-])=O.[Ce].[NH4+]>C(#N)C.O>[OH:7][CH2:8][C:9]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([C@@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[C:23]([NH:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])=[O:17])=[O:10]

Participants

6

Reactant 3

HCID 1049PyridineHCID 53792896(S)-2-[[(S)-2-[(p-Methoxyphenoxy)acetyl]-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamideHCID 57418452Ammonium cerium-nitrate

Product 1

HCID 178060Jtp-4819Yield 52.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(S)-2-[[(S)-2-[(p-Methoxyphenoxy)acetyl]-1-pyrrolidinyl] -carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide (500 mg) was dissolved in acetonitrile (8 ml) and water (2 ml), and thereto were added pyridine (0.22 ml) and ammonium cerium nitrate (1.47 g). The mixture was stirred at room temperature for 30 minutes. The mixture was poured into ice water and extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform-methanol) to give the title compound (203 mg) (see Table 1).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: chloroform-methanol)

Sources & evidence

ORD record
ord-84832c12fb0b49548dae270182355a3d
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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