Sodium Dithionite → HCID 178508026, compound

HRID 574672Notes

Reaction equation

HRID 574672 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[N:15]=[C:14]([OH:16])[C:13]([N+:17]([O-])=O)=[CH:12][N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C1COCC1.O>[NH2:17][C:13]1[C:14]([OH:16])=[N:15][C:10]([CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 178526812HCID 178526812, compound

Product 1

HCID 178508026HCID 178508026, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of step B product, 3-d, (25 g, crude) in THF/H2O (1000 mL, VTHF/VH2O=1:1) was added with Na2S2O4 (33.3 g, 191.6 mmol) and stirred at room temperature for 4 h. The reaction mixture was extracted with EA (1000 mL), washed with brine (200 mL), and concentrated in vacuum. The residue was purified by column chromatography to afford the product, 3-e, (7.8 g) as a white solid. 1H NMR (300 MHz, CDCl3): δ 4.42 (s, 2H), 4.63 (s, 2H), 7.33-7.36 (m, 6H). LC-MS (M+H)+ 232.1

Workup

  1. extractionThe reaction mixture was extracted with EA (1000 mL)
  2. washwashed with brine (200 mL)
  3. concentrationconcentrated in vacuum
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9347d6924a82483883bd29e72c1b5090
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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