Isobutyl chloroformate → HCID 178477369, 화합물

HRID 224907

반응식

HRID 224907 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:14][C:13]([CH2:15][C:16]([OH:18])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(Cl)=O)C(C)C.[C:27]1([CH:33]([O:40][C:41]([C:43]2[N:48]3[C:49](=[O:52])[C@@H:50]([NH2:51])[C@H:47]3[S:46][CH2:45][C:44]=2[CH:53]([S:55][C:56]2[NH:60][N:59]=[N:58][N:57]=2)[CH3:54])=[O:42])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl.CN1CCOCC1>[C:27]1([CH:33]([O:40][C:41]([C:43]2[N:48]3[C:49](=[O:52])[C@@H:50]([NH:51][C:16](=[O:18])[CH2:15][C:13]4[S:14][C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:11][CH:12]=4)[C@H:47]3[S:46][CH2:45][C:44]=2[CH:53]([S:55][C:56]2[NH:60][N:59]=[N:58][N:57]=2)[CH3:54])=[O:42])[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

참가 물질

6

반응물 3

HCID 62365Isobutyl chloroformateHCID 202932812-[5-({[(Tert-butoxy)carbonyl]amino}methyl)thiophen-2-yl]aceticacidHCID 178477368HCID 178477368, 화합물

생성물 1

HCID 178477369HCID 178477369, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 79724-Methylmorpholine용매

반응 조건

온도
-20 °C

실험 절차

5.43 g of 2-(5-tert.-butoxycarbonylaminomethyl-2-thienyl)-acetic acid are dissolved in 200 ml of methylene chloride containing 2.20 ml of 4-methyl-morpholine, the solution, from which moisture is kept excluded, is cooled to -20° C. and 2.86 ml of chloroformic acid isobutyl ester are added dropwise. After 30 minutes, a solution of 9.35 g of 7β-amino-3-(1-methyl-5-tetrazolylthiomethyl)-3-cephem-4-carboxylic acid diphenylmethyl ester in 100 ml of methylene chloride is added, after which stirring is continued for one hour at -20° C. and for 16 hours whilst slowly warming to room temperature. The mixture is poured out onto ice-cold water, the organic solution is separated off and the aqueous phase is again extracted with 100 ml of methylene chloride. The organic extracts are washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. Crystallisation of the residue from a mixture of methyl acetate and diethyl ether gives 7β-[2-(5-tert.-butoxycarbonylaminomethyl-2-thienyl)-acetylamino]-3-(1-methyl-5-tetrazolylthiomethyl)-3-cephem-4-carboxylic acid diphenylmethyl ester, thin layer chromatogram (silica gel): Rf= 0.38 (system: chloroform/ethyl acetate/acetic acid, 80:19:1); ultraviolet absorption spectrum (in 95% strength aqueous ethanol): shoulders at 242 mμ (ε=16,400) and 274 mμ (ε=9,200); infrared absorption spectrum (in mineral oil): characteristic bands at 3.03μ, 5.58μ, 5.79μ, 6.12μ and 6.51μ.

후처리

  1. waitis continued for one hour at -20° C. and for 16 hours
  2. temperaturewhilst slowly warming to room temperature
  3. additionThe mixture is poured out onto ice-cold water
  4. customthe organic solution is separated off
  5. extractionthe aqueous phase is again extracted with 100 ml of methylene chloride
  6. washThe organic extracts are washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated
  9. customCrystallisation of the residue
  10. additionfrom a mixture of methyl acetate and diethyl ether

출처 및 근거

ORD 기록
ord-183d416d11cb4b9b8cf349a7afd0e56b
출처 데이터셋
uspto-grants-1980_11
특허 번호
US04234578

연결된 노트

불러오는 중…