Chlorine → 4-Nitrobenzyl 3-(3-carboxyphenoxy)-2-(4(S)-chloro-3(S)-(1(R)-hydroxyethyl)azetidin-2-on-1-yl)-3-trimethylacetylthiopropenoate

HRID 231965

반응식

HRID 231965 반응식
[C:1]([C:4]1[CH:5]=[C:6]([CH:40]=[CH:41][CH:42]=1)[O:7][C:8]([C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])=[C:9]([N:23]1[C@H:26](SCC)[C@@H:25]([C@H:30]([OH:32])[CH3:31])[C:24]1=[O:33])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[S:11])([OH:3])=[O:2].[Cl:43]Cl>[2H]C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[C:1]([C:4]1[CH:5]=[C:6]([CH:40]=[CH:41][CH:42]=1)[O:7][C:8]([C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])=[C:9]([N:23]1[C@@H:26]([Cl:43])[C@@H:25]([C@H:30]([OH:32])[CH3:31])[C:24]1=[O:33])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[S:11])([OH:3])=[O:2]

참가 물질

5

반응물 2

HCID 24526ChlorineHCID 867432504-nitrobenzyl 3-(3-carboxyphenoxy)-2-(4(R)-ethylthio-3(S)-[1(R)-hydroxyethyl]azetidin-2-on-1-yl)-3-trimethylacetylthiopropenoate

생성물 1

HCID 867432494-Nitrobenzyl 3-(3-carboxyphenoxy)-2-(4(S)-chloro-3(S)-(1(R)-hydroxyethyl)azetidin-2-on-1-yl)-3-trimethylacetylthiopropenoate수율 87.3%

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 71583Chloroform-D용매

반응 조건

온도
-40 °C

실험 절차

To a stirred solution of 5.5 g of 4-nitrobenzyl 3-(3-carboxyphenoxy)-2-(4(R)-ethylthio-3(S)-[1(R)-hydroxyethyl]azetidin-2-on-1-yl)-3-trimethylacetylthiopropenoate in 50 ml of dry deuterochloroform at -40° C. was added a solution of 10.6 mmol of chlorine in carbon tetrachloride. The mixture was stirred for a further 30 minutes at -40° C., and for 30 minutes at room temperature, and was evaporated in vacuo. Chromatography of the residue over silica gel, and elution with hexane-ethyl acetate-formic acid mixtures afforded 4.6 g of the title compound.

후처리

  1. waitfor 30 minutes at room temperature
  2. customwas evaporated in vacuo
  3. washChromatography of the residue over silica gel, and elution with hexane-ethyl acetate-formic acid mixtures

출처 및 근거

ORD 기록
ord-8ff1eeab135845bdbb2d2bdae8541ff1
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04849419

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