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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Trifluoroacetic acid → (6R,7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-(1H-pyrazol-4-ylmethylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1274973
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HRID 1274973 반응식
FC(F)(F)C(O)=O.[NH2:8][C:9]1[S:10][C:11]([Cl:57])=[C:12](/[C:14](=[N:50]/[O:51]C2CCC=C2)/[C:15]([NH:17][C@@H:18]2[C:48](=[O:49])[N:20]3[C:21]([C:32]([O:34]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:33])=[C:22]([S:25][CH2:26][C:27]4[CH:28]=[N:29][NH:30][CH:31]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1.C1(OC)C=CC=CC=1.C(OC(C)C)(C)C>ClCCl>[NH2:8][C:9]1[S:10][C:11]([Cl:57])=[C:12](/[C:14](=[N:50]/[OH:51])/[C:15]([NH:17][C@@H:18]2[C:48](=[O:49])[N:20]3[C:21]([C:32]([OH:34])=[O:33])=[C:22]([S:25][CH2:26][C:27]4[CH:31]=[N:30][NH:29][CH:28]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1
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참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 88198442benzhydryl (6R,7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-cyclopent-2-en-1-yloxyiminoacetyl]amino]-8-oxo-3-(1H-pyrazol-4-ylmethylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

생성물 1

HCID 9871187
(6R,7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-(1H-pyrazol-4-ylmethylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
수율 35.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Under nitrogen atmosphere, trifluoroacetic acid (4.0 ml) was added dropwise to a solution of diphenylmethyl 7β-[2-(2-amino-5-chlorothiazol-4-yl)-2-(Z)-(2-cyclopenten-1-yloxyimino)acetamido]-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (1.71 g) in the mixture of dichloromethane (6.0 ml) and anisole (2.0 ml) at 0° C. Stirring was continued for 2 hours at the same temperature, the mixture was poured into isopropyl ether (200 ml). The resulting precipitate was collected by filtration, and then dissolved in the mixture of ethyl acetate and pH 6.86 buffer. The organic layer was removed, and the aqueous layer was adjusted pH 3.0 with 1N hydrochloric acid, concentrated in vacuo, then chlomatographed on a HP-20 column (eluent: water-methanol) to afford 7β-[2-(2-amino-5-chlorothiazol-4-yl)-2-(Z)-(hydroxyimino)acetamido]-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylic acid (418.3 mg).

후처리

  1. filtrationThe resulting precipitate was collected by filtration
  2. dissolutiondissolved in the mixture of ethyl acetate and pH 6.86 buffer
  3. customThe organic layer was removed
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3cfb3f25f0c64876901a46cd2ab2b909
출처 데이터셋
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06159961

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