Thionyl Chloride → Rac-benzyl-{1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]ethyl}carbamate

HRID 848123

반응식

HRID 848123 반응식
[C:1]([NH:11][CH:12]([C:14]([OH:16])=O)[CH3:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].S(Cl)(Cl)=O.[NH2:21][C:22]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][C:23]=1[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32])=[O:25]>O1CCCC1>[CH2:4]([O:3][C:1](=[O:2])[NH:11][CH:12]([C:14](=[O:16])[NH:21][C:22]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][C:23]=1[C:24](=[O:25])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32])[CH3:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

참가 물질

5

반응물 3

HCID 24386Thionyl ChlorideHCID 676572-Amino-2'-fluoro-5-nitrobenzophenoneHCID 95657N-(Benzyloxycarbonyl)-DL-alanine

생성물 1

HCID 20562333Rac-benzyl-{1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]ethyl}carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

50 g of carbobenzoxy-DL-alanine are dissolved in 400 ml of absolute tetrahydrofuran, treated dropwise while cooling with ice with 30 g of thionyl chloride and stirred for 40 minutes, a suspension of 50 g of 2-amino-5-nitro-2'-fluorobenzophenone in 200 ml of absolute tetrahydrofuran then being rapidly added dropwise. Subsequently, the mixture is stirred at room temperature for 18 hours, the solution is concentrated and the residue is treated with ice and 10% sodium bicarbonate solution. The mixture is extracted with methylene chloride, the organic solution is dried with sodium sulphate, filtered and concentrated. The residue is crystallised from ethanol and yields rac-benzyl-{1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]ethyl}-carbamate which is further processed directly as the crude product.

후처리

  1. additiontreated dropwise
  2. additionthen being rapidly added dropwise
  3. stirringSubsequently, the mixture is stirred at room temperature for 18 hours
  4. concentrationthe solution is concentrated
  5. additionthe residue is treated with ice and 10% sodium bicarbonate solution
  6. extractionThe mixture is extracted with methylene chloride
  7. dry with materialthe organic solution is dried with sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue is crystallised from ethanol

출처 및 근거

ORD 기록
ord-0f98b1f17cf4496c80eac146beee190a
출처 데이터셋
uspto-grants-1981_10
특허 번호
US04294758

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