Ethanol → HCID 66905116, compound

HRID 1967470Notes

Reaction equation

HRID 1967470 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:27]([O-])=O)[C:5]([NH:8][CH2:9][CH2:10][CH:11]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N:6][CH:7]=1.[Cl-].[NH4+].C(O)C>[Fe].O1CCCC1>[NH2:27][C:4]1[C:5]([NH:8][CH2:9][CH2:10][CH:11]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 66905396HCID 66905396, compound

Product 1

HCID 66905116HCID 66905116, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 3.5 g of tert-butyl 4-[(5-bromo-3-nitropyridin-2-yl)amino]-2-tert-butoxycarbonylaminobutanoate, 1.23 g (22 mmol) of iron powder and 20 g (0.373 mol) of ammonium chloride in 40 ml of a 1:1 mixture of ethanol and tetrahydrofuran is heated at reflux for two hours. After this time the reaction mixture is filtered on a bed of celite, which is rinsed with 100 ml of ethanol. The filtrate is concentrated under reduced pressure and then the residue is taken up in 20 ml of water. The mixture is then extracted with three times 50 ml of ethyl acetate. The organic phases are combined, washed with 50 ml of a saturated aqueous sodium chloride solution, dried over sodium sulfate and then concentrated under reduced pressure. An oil is recovered which is purified by chromatography on a silica column, eluting with a mixture of dichloromethane and methanol. This gives 2.93 g of the expected product in the form of a solid, used as it is in the remainder of the synthesis.

Workup

  1. temperatureis heated
  2. temperatureat reflux for two hours
  3. filtrationAfter this time the reaction mixture is filtered on a bed of celite, which
  4. washis rinsed with 100 ml of ethanol
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. extractionThe mixture is then extracted with three times 50 ml of ethyl acetate
  7. washwashed with 50 ml of a saturated aqueous sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customAn oil is recovered which
  11. customis purified by chromatography on a silica column
  12. washeluting with a mixture of dichloromethane and methanol
  13. customis in the remainder of the synthesis

Sources & evidence

ORD record
ord-74605eacc9ae4852a010e73e5199d623
Source dataset
uspto-grants-2013_04
Patent number
US08420817B2

Reaction notes

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