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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Phosphorus oxychloride → 7-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid

HRID 256430
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HRID 256430 반응식
P(Cl)(Cl)(Cl)=O.[CH:6]([NH:8][C:9]1[S:10][C:11]([Br:21])=[C:12]([C:14](=[N:18][O:19][CH3:20])[C:15]([OH:17])=O)[N:13]=1)=[O:7].[NH2:22][CH:23]1[C:41](=[O:42])[N:25]2[C:26]([C:38]([OH:40])=[O:39])=[C:27]([CH2:30][S:31][C:32]3[S:33][C:34]([CH3:37])=[N:35][N:36]=3)[CH2:28][S:29][C@H:24]12.C[Si](CC(N)=O)(C)C>C(OCC)(=O)C.O.CN(C)C=O>[CH:6]([NH:8][C:9]1[S:10][C:11]([Br:21])=[C:12]([C:14](=[N:18][O:19][CH3:20])[C:15]([NH:22][CH:23]2[C:41](=[O:42])[N:25]3[C:26]([C:38]([OH:40])=[O:39])=[C:27]([CH2:30][S:31][C:32]4[S:33][C:34]([CH3:37])=[N:35][N:36]=4)[CH2:28][S:29][C@H:24]23)=[O:17])[N:13]=1)=[O:7]
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참가 물질

8

반응물 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 129420347-Amino-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acidHCID 538011022-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acid

생성물 1

HCID 1317153357-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid
수율 59.2%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매4회

실험 절차

A mixture of dimethylformamide (0.3 ml.), phosphoryl chloride (0.35 ml.) and dry ethyl acetate (1.5 ml.) was stirred for 30 minutes under ice-cooling. Dry ethyl acetate (1.5 ml.) and 2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 1.0 g.) were added to the solution and stirred for 50 minutes under ice-cooling. The solution was added dropwise to a chilled solution of 7-amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (1.1 g.) and trimethylsilylacetamide (2.5 g.) in dry ethyl acetate (30 ml.), and stirred at -20° to -10° C. for an hour. To the reaction mixture were added ethyl acetate (30 ml.) and water 20 ml., and the insoluble substance was filtered off. The ethyl acetate layer was separated from the filtrate, and the aqueous layer was washed with ethyl acetate. The washings and the ethyl acetate layer were combined together, washed with a saturated aqueous sodium chloride, dried over magnesium sulfate and then evaporated in vacuo. The residue was pulverized with diethyl ether, and the precipitates were collected by filtration, washed with diethyl ether and dried to give 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer, 1.2 g.).

후처리

  1. temperaturecooling
  2. stirringstirred for 50 minutes under ice-
  3. temperaturecooling
  4. stirringstirred at -20° to -10° C. for an hour
  5. filtration, and the insoluble substance was filtered off
  6. customThe ethyl acetate layer was separated from the filtrate
  7. washthe aqueous layer was washed with ethyl acetate
  8. washwashed with a saturated aqueous sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. customevaporated in vacuo
  11. filtrationthe precipitates were collected by filtration
  12. washwashed with diethyl ether
  13. customdried

출처 및 근거

ORD 기록
ord-83bf85e407d849f1a1fd1174db27c2cf
출처 데이터셋
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04703046

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