Tin dichloride dihydrate → HCID 66993362, compound

HRID 1953529Notes

Reaction equation

HRID 1953529 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:35])/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-])=O)[CH:27]=3)=[CH:4][C:3]=2[O:2]1.Cl[Sn]Cl.O>CCO>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:35])/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([NH2:32])[CH:27]=3)=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 43835034Tin dichloride dihydrateHCID 66993236HCID 66993236, compound

Product 1

HCID 66993362HCID 66993362, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Example 60 (1.36 g, 2.9 mmol), SnCl2.H2O (2.8 g, 5 equiv.) in EtOH was refluxed overnight. After evaporation of the solvent, the residue was taken up in 50 mL of NaOH (1N). The aqueous phase was extracted with 2×100 mL of DCM and 2×50 mL of EtOAc. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. Flash chromatography (SiO2, DCM:MeOH (95:5) and recrystallization from EtOH:DCM gave the title compound (0.27 g, 21%) as a pale yellow powder.

Workup

  1. customAfter evaporation of the solvent
  2. extractionThe aqueous phase was extracted with 2×100 mL of DCM and 2×50 mL of EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customFlash chromatography (SiO2, DCM:MeOH (95:5) and recrystallization from EtOH

Sources & evidence

ORD record
ord-efc81384619749dfbb309e4434961fb4
Source dataset
uspto-grants-2000_09
Patent number
US06117881

Reaction notes

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