Methanol → HCID 131732766, compound

HRID 1474429Notes

Reaction equation

HRID 1474429 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([N:12]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:5]([CH3:27])[CH:4]=1)#[N:2].S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].CO>C1COCC1.O>[NH2:9][C:7]1[CH:8]=[C:3]([C:1]#[N:2])[CH:4]=[C:5]([CH3:27])[C:6]=1[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:20]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21]

Participants

7

Reactant 4

HCID 887Methanol2×HCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 131732765HCID 131732765, compound

Product 1

HCID 131732766HCID 131732766, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Di-t-butyl (4-cyano-2-methyl-6-nitrophenyl)imidodicarbonate obtained in Step 1 (3.77 g, 10 mmol) was dissolved in THF (0.2 M, 50 mL), and a solution prepared by dissolving sodium hydrosulfite (15.7 g, 9 eq, 90 mmol) and sodium bicarbonate (7.56 g, 90 mmol) in H2O (0.1 M, 100 mL) was added thereto. Subsequently, MeOH (17 mL) was added to the mixture, which was then stirred at room temperature for 1 hour. Upon completion of the reaction, THF and MeOH were removed under reduced pressure, and the residue was added with brine and extracted with ethyl acetate. The organic layer thus obtained was dried over MgSO4 and concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography (EA:Hex=1:2) to obtain the title compound in a white solid (2.90 g, yield: 83%).

Workup

  1. customa solution prepared
  2. additionwas added
  3. customwere removed under reduced pressure
  4. additionthe residue was added with brine
  5. extractionextracted with ethyl acetate
  6. customThe organic layer thus obtained
  7. dry with materialwas dried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customThen, the residue was purified by silica gel column chromatography (EA:Hex=1:2)

Sources & evidence

ORD record
ord-6196e78a8e524f0192fae99cad5c0177
Source dataset
uspto-grants-2015_04
Patent number
US09018233B2

Reaction notes

Loading…