Stannous Chloride → HCID 21101496, compound

HRID 1353038Notes

Reaction equation

HRID 1353038 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][CH:29]=1)[C:7]([NH:9][CH2:10][C:11]([NH:13][CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:12])=[O:8])([O-])=O.[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][CH:29]=1)[C:7]([NH:9][CH2:10][C:11]([NH:13][CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:12])=[O:8]

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 20745454HCID 20745454, compound

Product 1

HCID 21101496HCID 21101496, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3-{2-[(3-(nitro)benzoyl)amino]acetamido}-3-phenyl-propanoate from II.3a (2.7 g) in 100 ml of ethanol was treated with Tin(II) chloride (7.6 g) and heated under reflux for 3 h. The reaction mixture was then added to ice, rendered neutral with NaHCO3 solution and filtered through Celite. The filtrate was extracted with methylene chloride, dried (MgSO4) and concentrated. Chromatographic purification (purification (methylene chloride/methanol (5:1)) yielded the product (yield: 2.0 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 h
  3. additionThe reaction mixture was then added to ice
  4. filtrationfiltered through Celite
  5. extractionThe filtrate was extracted with methylene chloride
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customChromatographic purification (
  9. custompurification (methylene chloride/methanol (5:1))

Sources & evidence

ORD record
ord-4c8aa8842e9d4762badfa525e7fb0c74
Source dataset
uspto-grants-2007_05
Patent number
US07220824B1

Reaction notes

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