Thionyl Chloride → Benzyl-rac-{1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]butyl}carbamate

HRID 848135

반응식

HRID 848135 반응식
[C:1]([NH:11][CH:12]([C:17]([OH:19])=O)[CH2:13][CH2:14][CH2:15]C)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].S(Cl)(Cl)=O.[NH2:24][C:25]1[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][C:26]=1[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[F:35])=[O:28]>O1CCCC1>[CH2:4]([O:3][C:1](=[O:2])[NH:11][CH:12]([C:17](=[O:19])[NH:24][C:25]1[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][C:26]=1[C:27](=[O:28])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[F:35])[CH2:13][CH2:14][CH3:15])[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 263476N-[(Benzyloxy)carbonyl]norleucine

생성물 1

HCID 131712305Benzyl-rac-{1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]butyl}carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

19.7 g of N-carbobenzoxy-DL-norleucine are dissolved in 200 ml of absolute tetrahydrofuran, the solution is treated dropwise while cooling with ice with 10 g of thionyl chloride and then stirred for 1 hour. To this solution there is rapidly added dropwise a solution of 17 g (0.065 M) of 2-amino-5-nitro-2'-fluorobenzophenone in 130 ml of absolute tetrahydrofuran and the mixture is then stirred at room temperature for 60 hours. The solution is concentrated and the residue is treated with ice and 10% sodium bicarbonate solution and extracted with methylene chloride. The organic solution is dried with sodium sulphate, filtered and concentrated. The residue is purified on a 450 g silica gel column using methylene chloride as the eluting agent and crystallised from ethanol. There is obtained benzyl-rac-{1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]butyl}carbamate which melts at 148°-150° C.

후처리

  1. additionthe solution is treated dropwise
  2. stirringthe mixture is then stirred at room temperature for 60 hours
  3. concentrationThe solution is concentrated
  4. additionthe residue is treated with ice and 10% sodium bicarbonate solution
  5. extractionextracted with methylene chloride
  6. dry with materialThe organic solution is dried with sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified on a 450 g silica gel column
  10. customcrystallised from ethanol

출처 및 근거

ORD 기록
ord-cc1e2d0aad534da1b8c06678a426964d
출처 데이터셋
uspto-grants-1981_10
특허 번호
US04294758

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