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Phosphorus pentachloride → 7-[2-Ethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate

HRID 1163879
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HRID 1163879 반응식
[CH2:1]([O:3][N:4]=[C:5]([C:9]1[N:10]=[C:11]([NH:14][CH:15]=[O:16])[S:12][CH:13]=1)[C:6]([OH:8])=O)[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl.C[Si](C)(C)NC(=O)C.O.O.Cl.[Cl-].[NH2:35][CH:36]1[C:53](=[O:54])[N:38]2[C:39]([C:50]([OH:52])=[O:51])=[C:40]([CH2:43][N+:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH2:41][S:42][C@H:37]12>ClCCl.O1CCCC1.C(OCC)(=O)C.O.C(N(CC)CC)C>[CH2:1]([O:3][N:4]=[C:5]([C:9]1[N:10]=[C:11]([NH:14][CH:15]=[O:16])[S:12][CH:13]=1)[C:6]([NH:35][CH:36]1[C:53](=[O:54])[N:38]2[C:39]([C:50]([O-:52])=[O:51])=[C:40]([CH2:43][N+:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH2:41][S:42][C@H:37]12)=[O:8])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 4

HCID 24819Phosphorus pentachlorideHCID 25989Acetamide, N-(trimethylsilyl)-HCID 544580772-(2-Formamidothiazol-4-yl)-2-ethoxyiminoacetic acidHCID 70450238HCID 70450238, 화합물

생성물 1

HCID 1317129237-[2-Ethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate수율 39.3%

시약·촉매·용매

5
HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

2-Ethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (2.2 g) was added to a solution of phosphorus pentachloride (2.0 g) in dichloromethane (40 ml) at -10° C., and stirred at -5° C. to -10° C. for 1 hour. After the addition of triethylamine (2.0 g), the resulting mixture was stirred at -5° C. for 5 minutes [Solution A]. N-trimethylsilylacetamide (9.8 g) was added to a stirred suspension of 1-[(7-amino-4-carboxy-3-cephem-3-yl)methyl]pyridinium chloride hydrochloride dihydrate (3.0 g) in dry tetrahydrofuran (60 ml), and the mixture was stirred for 20 minutes at 35° C. to 40° C. To the solution was added the solution A at -10° C. and the resulting solution was stirred at the same temperature for 40 minutes. Water and ethyl acetate were added to the reaction mixture at -10° C. and the separated aqueous layer was washed with ethyl acetate and adjusted to pH 4.0 with 10% aqueous solution of sodium hydroxide. The resulting solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark: Prepared by Mitsubishi Chemical Industries) and eluted with 10% aqueous solution of isopropyl alcohol. The fractions containing the object compound were collected and concentrated and lyophilized to give 7-[2-ethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (1.52 g).

후처리

  1. stirringthe mixture was stirred for 20 minutes at 35° C. to 40° C
  2. stirringthe resulting solution was stirred at the same temperature for 40 minutes
  3. washthe separated aqueous layer was washed with ethyl acetate
  4. customThe resulting solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark: Prepared by Mitsubishi Chemical Industries)
  5. washeluted with 10% aqueous solution of isopropyl alcohol
  6. additionThe fractions containing the object compound
  7. customwere collected
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c95f5b576d244dff86f896a36031c7bf
출처 데이터셋
uspto-grants-1983_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04367228

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