Benzyloxycarbonylglycine → Benzyl{[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]methyl}carbamate

HRID 848141

Reaction equation

HRID 848141 reaction equation
[C:1]([NH:11][CH2:12][C:13]([OH:15])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].S(Cl)(Cl)=O.[NH2:20][C:21]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][C:22]=1[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[F:31])=[O:24]>O1CCCC1>[CH2:4]([O:3][C:1](=[O:2])[NH:11][CH2:12][C:13](=[O:15])[NH:20][C:21]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][C:22]=1[C:23](=[O:24])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[F:31])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 14349BenzyloxycarbonylglycineHCID 24386Thionyl ChlorideHCID 676572-Amino-2'-fluoro-5-nitrobenzophenone

Product 1

HCID 20562352Benzyl{[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]methyl}carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

45 g of carbobenzoxy-glycine dissolved in 1 liter of absolute tetrahydrofuran are treated dropwise while cooling with ice with 20 ml of thionyl chloride and stirred for 1 hour while cooling with ice. There is then rapidly added dropwise thereto a suspension of 50 g of 2-amino-5-nitro-2'-fluorobenzophenone in 200 ml of absolute tetrahydrofuran and the mixture is stirred at room temperature for 18 hours. The solution obtained is concentrated and the residue is treated with ice and 10% sodium bicarbonate solution and extracted with methylene chloride. The organic solution is dried over sodium sulphate, filtered and concentrated. The residue is dissolved in a small amount of hot ethyl acetate, concentrated partially and treated with ether. Benzyl{[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]methyl}-carbamate is obtained. The mother liquors are purified on a 100 g silica gel column using methylene chloride as the eluting agent, an additional amount of the aforementioned product being obtained.

Workup

  1. additionare treated dropwise
  2. temperaturewhile cooling with ice
  3. additionThere is then rapidly added dropwise
  4. stirringthe mixture is stirred at room temperature for 18 hours
  5. customThe solution obtained
  6. concentrationis concentrated
  7. additionthe residue is treated with ice and 10% sodium bicarbonate solution
  8. extractionextracted with methylene chloride
  9. dry with materialThe organic solution is dried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. dissolutionThe residue is dissolved in a small amount of hot ethyl acetate
  13. concentrationconcentrated partially
  14. additiontreated with ether

Sources & evidence

ORD record
ord-473149f8530a4ff5aa4d9fb72addd08d
Source dataset
uspto-grants-1981_10
Patent number
US04294758

Linked notes

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