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

HRID 848141

반응식

HRID 848141 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-473149f8530a4ff5aa4d9fb72addd08d
출처 데이터셋
uspto-grants-1981_10
특허 번호
US04294758

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