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

HRID 848141

反応式

HRID 848141 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-473149f8530a4ff5aa4d9fb72addd08d
出典データセット
uspto-grants-1981_10
特許番号
US04294758

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