HCID 86707879, compound → HCID 86707878, compound

HRID 588995Notes

Reaction equation

HRID 588995 reaction equation
COC1C=CC(C[N:8]2[C:12](=[O:13])[C@@:11]3([CH2:25][C:16]4=[N:17][CH:18]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[CH:20]=[C:15]4[CH2:14]3)[N:10]([CH3:26])[C:9]2=[O:27])=CC=1>CO>[CH3:26][N:10]1[C@:11]2([CH2:25][C:16]3=[N:17][CH:18]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[CH:20]=[C:15]3[CH2:14]2)[C:12](=[O:13])[NH:8][C:9]1=[O:27]

Participants

3

Reactant 1

HCID 86707879HCID 86707879, compound

Product 1

HCID 86707878HCID 86707878, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl (6R)-1′-(4-methoxybenzyl)-3′-methyl-2′,5′-dioxo-5,7-dihydrospiro[cyclopenta[b]pyridine-6,4′-imidazolidine]-3-carboxylate (10.0 g, 25.3 mmol) in MeOH (100 mL) at ambient temperature was added ceric ammonium nitrate (27.7 g, 50.6 mmol) and the reaction mixture was stirred at ambient temperature for 18 h. The resulting mixture was partitioned between H2O (500 mL) and EtOAc (1 L) and the organic layer was discarded. The aqueous layer was adjusted to pH=7-8 by addition of 1 N aqueous NaOH and extracted further with EtOAc (2×500 mL) and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude solid was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH-100:0 to 90:10, to give the title compound. MS: m/z=276.1 (M+1).

Workup

  1. customThe resulting mixture was partitioned between H2O (500 mL) and EtOAc (1 L)
  2. additionThe aqueous layer was adjusted to pH=7-8 by addition of 1 N aqueous NaOH
  3. extractionextracted further with EtOAc (2×500 mL)
  4. dry with materialthe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude solid was purified by silica gel chromatography
  8. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-7731cd53c49a4ca4bac322f9e3cdbf44
Source dataset
uspto-grants-2016_01
Patent number
US09227973B2

Reaction notes

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